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

HRID 1518304
Notes
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Reaction equation

HRID 1518304 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[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:35]#[C:36][CH2:37][OH:38])=[C:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[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[N:10]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:44])([CH3:45])[CH3:46])[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]([CH2:35][CH2:36][CH2:37][OH:38])=[C:26]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 59447612tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxyprop-1-ynyl)thiazole-4-carboxylate

Product 1

HCID 59447663tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst
HCID 8857
Ethyl Acetate
Solvent

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 (38D) (2.0 g, 3.96 mmol) in EtOAc (20 mL) was added PtO2 (240 mg, 1.1 mmol). The mixture was stirred at rt under hydrogen (balloon) overnight. The mixture was then filtered and the filtrate was concentrated under reduced pressure to provide the desired product 38E: 1H NMR (300 MHz, CDCl3) δ ppm 8.30 (1H, m), 7.71 (1H, d), 7.59 (1H, m), 7.49 (1H, m), 7.35 (3H, m), 6.00 (2H, s), 5.14 (2H, s), 3.95 (2H, m), 3.75 (2H, t), 3.63 (2H, m), 3.17 (2H, t), 3.07 (2H, t), 2.40 (1H, t), 1.89 (2H, m), 1.58 (9H, d), 0.98 (2H, t), 0.01 (9H, m). MS (ESI(+)): m/z 681 (M+H).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b044092ad0c74968aa04df6c3ee590f6
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08232273B2

Reaction notes

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