Sodium hydride → HCID 178473776, compound

HRID 1846809

Reaction equation

HRID 1846809 reaction equation
[H-].[Na+].Cl.[S:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH:13][C@@H:14]1[CH2:17][C@H:16]([OH:18])[CH2:15]1.F[C:20]1[C:25]([C:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH:27]=2)=[CH:24][CH:23]=[CH:22][N:21]=1>CN(C)C=O.CCOC(C)=O>[S:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH:13][C@@H:14]1[CH2:15][C@H:16]([O:18][C:20]2[C:25]([C:26]3[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH:27]=3)=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:17]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 593269651-(4-(2-fluoropyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanoneHCID 178479706HCID 178479706, compound

Product 1

HCID 178473776HCID 178473776, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride, 60% dispersion in mineral oil (0.13 g, 3.18 mmol) was added to a solution of cis-3-(benzo[d]thiazol-2-ylamino)cyclobutanol hydrochloride (0.20 g, 0.795 mmol) in N,N-dimethylformamide (2.7 mL) under argon and the mixture was stirred for 30 min at RT. 1-(4-(2-Fluoropyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (0.17 g, 0.79 mmol) was next added, and the resulting mixture was heated at 100° C. for 2 h. The cooled reaction was diluted with EtOAc and washed with water. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Flash column chromatography (20% to 80% EtOAc/Hexanes) afforded 1-(4-(2-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutoxy)pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone as an off-white amorphous solid. [M+1]=421.0.

Workup

  1. temperaturethe resulting mixture was heated at 100° C. for 2 h
  2. customThe cooled reaction
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ce7c31a87d44015a6703483214b3fde
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Linked notes

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