Sodium Bicarbonate → 7-(6-Chloro-indole-1-sulfonyl)4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline

HRID 22824Notes

Reaction equation

HRID 22824 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:23]=[C:22]3[C:17]([C:18]([CH3:28])([CH3:27])[CH2:19][N:20](C(=O)C)[CH2:21]3)=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+]>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:23]=[C:22]3[C:17]([C:18]([CH3:28])([CH3:27])[CH2:19][NH:20][CH2:21]3)=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 225920261-[7-(6-Chloro-indole-1-sulfonyl)-4,4-dimethyl-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone

Product 1

HCID 101994437-(6-Chloro-indole-1-sulfonyl)4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline

Procedure

1-[7-(6-Chloro-indole-1-sulfonyl)-4,4-dimethyl-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone (D4) was N-deacetylated as described in Example 1 to afford, after treatment with sodium hydrogen carbonate solution, the title compound (E28). Treatment of a solution of this material in dichloromethane/diethyl ether with oxalic acid (1.5 equivalents) afforded the corresponding crystalline oxalate salt (65 mg, 42%), δH (CD3OD)/ppm 1.13 (6H, s), 2.71 (2H, br,s), 3.86 (2H, br,s), 6.61 (1H, d, J=3.7 Hz), 7.12 (1H, dd, J=8.4, 1.8 Hz), 7.40-7.86 (4H, m), 7.86 (1H, d, J=1.7 Hz). MS: m/z (MH30) 375/377.

Workup

  1. customto afford

Sources & evidence

ORD record
ord-055b3e613c69402393df9f5672cafdfa
Source dataset
uspto-grants-2005_02
Patent number
US06849644B2

Reaction notes

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