Dimethylformamide → 2-(1-(Benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-5-(3-phenoxypropyl)thiazole-4-carboxylic acid

HRID 1641069Notes

Reaction equation

HRID 1641069 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][C:11]1[S:15][C:14]([C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][CH2:22][NH:23]3)=[CH:18][CH:17]=2)=[N:13][C:12]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[C:32]1[NH:40][C:41]([N:43]1[CH:47]=[CH:46]N=[CH:44]1)=[O:42].CN(C=O)C>CCOC(C)=O>[S:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[C:32]1[NH:40][C:41]([N:23]1[C:24]2[C:19](=[CH:18][CH:17]=[C:16]([C:14]3[S:15][C:11]([CH2:10][CH2:9][CH2:8][O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[C:12]([C:26]([OH:28])=[O:27])[N:13]=3)[CH:25]=2)[CH2:20][CH2:21][CH2:22]1)=[O:42].[S:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[C:32]1[NH:40][C:41]([N:43]1[C:44]2[C:19](=[CH:18][CH:17]=[C:16]([C:14]3[S:15][C:11]([CH2:10][CH2:9][CH2:8][O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[C:12]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:13]=3)[CH:25]=2)[CH2:20][CH2:46][CH2:47]1)=[O:42]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 59418727N-(benzo[d]thiazol-2-yl)-1H-imidazole-1-carboxamideHCID 59418748Ethyl 5-(3-phenoxypropyl)-2-(1,2,3,4-tetrahydroquinolin-7-yl)thiazole-4-carboxylate

Product 2

HCID 468405212-(1-(Benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-5-(3-phenoxypropyl)thiazole-4-carboxylic acidHCID 86643666Ethyl 2-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-5-(3-phenoxypropyl)thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound 2-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-5-(3-phenoxypropyl)thiazole-4-carboxylic acid (24) was prepared by the following procedure: To ethyl 5-(3-phenoxypropyl)-2-(1,2,3,4-tetrahydroquinolin-7-yl)thiazole-4-carboxylate (24A) (18 mg, 0.0.42 mmol) and N-(benzo[d]thiazol-2-yl)-1H-imidazole-1-carboxamide (1M) (10 mg, 0.042 mmol) was added DMF (2 mL) and stirred at rt overnight. The reaction mixture was diluted with EtOAc, washed sequentially with NaHCO3, water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure to provide ethyl 2-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-5-(3-phenoxypropyl)thiazole-4-carboxylate. LC/MS (APCI): m/z 599.5 (M+H).

Workup

  1. washwashed sequentially with NaHCO3, water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f42e7d8d4e764bd894bedf90a1fcb0ec
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

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