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2-Chlorobenzothiazole → HCID 178517872, compound

HRID 707408
Notes
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Reaction equation

HRID 707408 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[C:9]([F:18])([F:17])[C:8]2=[O:19])[CH2:4]1.Cl[C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.C(N(CC)C(C)C)(C)C>CS(C)=O.O>[S:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[NH:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[C:9]([F:18])([F:17])[C:8]2=[O:19])[CH2:4]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 119872-ChlorobenzothiazoleHCID 81531DiisopropylethylamineHCID 178479281HCID 178479281, compound

Product 1

HCID 178517872HCID 178517872, compoundYield 22.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 962
Water
Solvent

Conditions

Temperature
120 °C

Procedure

1-(Trans-3-aminocyclobutyl)-3,3,5-trifluoro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one hydrochloride (0.105 g, 0.358 mmol), 2-chlorobenzothiazole (0.0728 g, 0.429 mmol), and N,N-diisopropylethylamine (0.249 mL, 1.430 mmol) were mixed in DMSO (0.5 mL) in a sealed tube. The reaction mixture was stirred at 120° C. for 1.5 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography eluting with EtOAc in hexanes to yield the title compound (0.032 g, 0.082 mmol, 22.9% yield) as a white solid. M+1: 391.1 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.46-2.56 (m, 2 H) 3.37-3.48 (m, 2 H) 4.58 (m, J=3.50 Hz, 1 H) 5.23 (quin, J=8.61 Hz, 1 H) 5.76 (br. s., 1 H) 7.12 (t, J=7.53 Hz, 1 H) 7.32 (t, J=7.73 Hz, 1 H) 7.56-7.66 (m, 3 H) 8.30 (s, 1 H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was purified by silica gel column chromatography
  9. washeluting with EtOAc in hexanes

Sources & evidence

ORD record
ord-dbaab103664a47b7a7189afc753922b3
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174992B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes