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Methanol → Ethyl 4-allyl-1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate

HRID 712295
Notes
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Reaction equation

HRID 712295 reaction equation
[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:7][C:6]=2[CH:5]=[C:4](I)[CH:3]=1.[CH2:18]([C:21]1([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:26][CH2:25][N:24]([C:27]2[N:32]=[CH:31][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][N:28]=2)[CH2:23][CH2:22]1)[CH:19]=[CH2:20].CO.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[CH2:18]([C:21]1([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:22][CH2:23][N:24]([C:27]2[N:28]=[CH:29][C:30]([C:4]3[CH:3]=[C:2]([Br:1])[C:10]4[S:9][C:8]([NH:11][C:12](=[O:13])[NH:14][CH2:15][CH3:16])=[N:7][C:6]=4[CH:5]=3)=[CH:31][N:32]=2)[CH2:25][CH2:26]1)[CH:19]=[CH2:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 887MethanolHCID 62657Potassium Phosphate, TribasicHCID 578137231-(7-Bromo-5-iodobenzo[d]thiazol-2-yl)-3-ethylureaHCID 66976919Ethyl 4-allyl-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperidine-4-carboxylate

Product 1

HCID 86664009Ethyl 4-allyl-1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate
Yield 27%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(7-bromo-5-iodobenzothiazol-2-yl)-3-ethylurea (0.55 g, 1.29 mmol) and ethyl 4-allyl-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperidine-4-carboxylate (0.79 g, 1.97 mmol) in 1,4-dioxane:MeOH (30:20 mL) was added potassium phosphate (0.41 g, 1.97 mmol) at rt and the mixture degassed for 15-20 min by purging N2 followed by addition of tetrakis(triphenylphosphine)palladium(0) (0.15 g, 0.13 mmol). The reaction mixture was again degassed for another 15-20 min then heated up to 80° C. for 5 h. After completion of reaction (by TLC), the reaction mixture was cooled to rt, diluted with EtOAc (500 mL) and passed through celite. The filtrate was evaporated and the crude residue was purified over 100-200 M silica-gel using 1.50% MeOH: DCM to obtain the desired product as a beige solid (0.20 g, 27% yield). 1H NMR (DMSO-d6): δ 1.09 (t, J=7.20 Hz, 3H), 1.21 (t, J=6.80 Hz, 3H), 1.47 (m, 2H), 2.05 (m, 2H), 2.29 (m, 2H), 3.18 (m, 2H), 3.21 (q, J=7.20, 2H), 4.17 (q, J=6.80 Hz, 2H), 4.46 (m, 2H), 5.05 (m, 2H), 5.72 (m, 1H) 6.74 (br s, 1H), 7.69 (s, 1H), 7.87 (s, 1H); 8.77 (s, 2H) and 10.90 (br s, 1H).

Workup

  1. customthe mixture degassed for 15-20 min
  2. customby purging N2
  3. customThe reaction mixture was again degassed for another 15-20 min
  4. customAfter completion of reaction (by TLC)
  5. temperaturethe reaction mixture was cooled to rt
  6. customThe filtrate was evaporated
  7. customthe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-c6b56068507a4de092cffa9d98f5007e
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181234B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes