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

HRID 2178232
Notes
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Reaction equation

HRID 2178232 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 acid
HCID 86643666
Ethyl 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 (M) (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-ca15e67fa3f24c3bbd2062a9e29ffd06
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09067928B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes