2-Chloromethyl 2-(trimethylsilyl)ethyl ether → ethyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-bromothiazole-4-carboxylate

HRID 1518291Notes

Reaction equation

HRID 1518291 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]([Br:33])=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[CH3:34][Si:35]([CH2:38][CH2:39][O:40][CH2:41]Cl)([CH3:37])[CH3:36]>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:41][O:40][CH2:39][CH2:38][Si:35]([CH3:37])([CH3:36])[CH3:34])[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]([Br:33])=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

4

Reactant 2

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 59447489ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-bromothiazole-4-carboxylate

Product 1

HCID 59447650ethyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-bromothiazole-4-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of compound 34B (0.815 g, 1.5 mmol) and SEMCl (0.318 mL, 1.8 mmol) in THF (6 mL) was added TEA (0.65 mL, 4.5 mmol) at rt. The reaction mixture was stirred for 20 minutes, concentrated under reduced pressure, and purified by column chromatography on silica gel eluting with 3:1/hexanes:EtOAc to provide 0.95 g of the desired product as a mixture of two inseparable isomers: MS (ESI(+)): m/z 657 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by column chromatography on silica gel eluting with 3:1/hexanes

Sources & evidence

ORD record
ord-2540a13d00aa4149b150da742b5a4108
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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