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Ethyl chloroformate → HCID 54761161, compound

HRID 929963
Notes
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Reaction equation

HRID 929963 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=O)=[N:12][CH:13]=2)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.ClC(OCC)=O.[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]([NH:42][C:43]2[CH:47]=[C:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[O:45][N:44]=2)=[O:41])=[CH:35][CH:34]=1>C(Cl)Cl>[C:48]([C:46]1[O:45][N:44]=[C:43]([NH:42][C:40](=[O:41])[NH:39][C:36]2[CH:35]=[CH:34][C:33]([NH:32][C:14](=[O:16])[C:11]3[CH:10]=[CH:9][C:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)=[CH:13][N:12]=3)=[CH:38][CH:37]=2)[CH:47]=1)([CH3:51])([CH3:49])[CH3:50]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 57440396HCID 57440396, compoundHCID 59380899HCID 59380899, compound

Product 1

HCID 54761161HCID 54761161, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a stirred solution of 5-(4-methylpiperazin-1-yl)picolinic acid (185 mg, 0.46 mmol) in 5 mL of DCM was added DIEA (82 μL, 0.46 mmol) and ethyl chloroformate (45 μL, 0.46 mmol). The resulting mixture was stirred at rt for 15 min, sonicated for 10 min. 1-(4-Aminophenyl)-3-(5-tert-butylisoxazol-3-yl)urea (128 mg, 0.46 mmol) was added. The resulting mixture was refluxed for 30 min. LC-MS indicated the reaction mostly done. Solvent was then removed under reduced pressure and residue was purified on reverse phase HPLC to give N-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenyl)-5-(4-methylpiperazin-1-yl)picolinamide (65 mg, 29%) as a white foamy solid. LC-MS (ESI) m/z 478 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 9.48 (s, 1H), 8.79 (s, 1H), 8.36 (d, J=2.45 Hz, 1H), 7.96 (d, J=8.85 Hz, 1H), 7.80 (d, J=8.85 Hz, 2H), 7.47 (dd, J=2.64, 8.85 Hz, 1H), 7.41 (d, J=9.04 Hz, 2H), 6.50 (s, 1H), 3.35 (br. s., 8H), 2.26 (s, 3H), 1.30 (s, 9H).

Workup

  1. customsonicated for 10 min
  2. temperatureThe resulting mixture was refluxed for 30 min
  3. customthe reaction
  4. customSolvent was then removed under reduced pressure and residue
  5. customwas purified on reverse phase HPLC

Sources & evidence

ORD record
ord-2380a83005344940b7fb7b18f37fb852
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296722B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes