methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxyprop-1-ynyl)thiazole-4-carboxylate → methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-carboxylate

HRID 1518277Notes

Reaction equation

HRID 1518277 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([C:32]#[C:33][CH2:34][OH:35])=[C:26]([C:28]([O:30][CH3:31])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]>CCOC(C)=O.O=[Pt]=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:32][CH2:33][CH2:34][OH:35])=[C:26]([C:28]([O:30][CH3:31])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

4

Reactant 1

HCID 59447607methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxyprop-1-ynyl)thiazole-4-carboxylate

Product 1

HCID 59447541methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxyprop-1-ynyl)thiazole-4-carboxylate (8D) (1.2 g, 2.31 mmol) in EtOAc (20 mL) was added PtO2 (120 mg, 0.53 mmol). The mixture was stirred at rt under a hydrogen balloon overnight. After this time the mixture was filtered and the filtrate was concentrated to provide the desired product methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-carboxylate (8E): LC/MS (APCI): m/z 509.2 (M+H).

Workup

  1. filtrationAfter this time the mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-abffd1f4be324904a5b26c3a3c2de13e
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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