Ammonia → HCID 57508932, compound

HRID 1665976Notes

Reaction equation

HRID 1665976 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:27])[CH2:9][CH2:10][C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([CH2:18][CH2:19][CH2:20]OS(C)(=O)=O)=[C:13]([CH3:26])[CH:12]=2)=[C:5]2[CH2:28][CH2:29][C:30]([CH3:33])([CH3:32])[CH2:31][C:4]=12)[CH3:2].[NH3:34]>CO>[NH2:34][CH2:20][CH2:19][CH2:18][C:14]1[C:15]([CH3:17])=[CH:16][C:11]([CH2:10][CH2:9][C:8]([C:6]2[S:7][C:3]([CH2:1][CH3:2])=[C:4]3[CH2:31][C:30]([CH3:33])([CH3:32])[CH2:29][CH2:28][C:5]=23)=[O:27])=[CH:12][C:13]=1[CH3:26]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57508931HCID 57508931, compound

Product 1

HCID 57508932HCID 57508932, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methanesulfonic acid 3-{4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2,6-dimethyl-phenyl}-propyl ester (160 mg, 0.326 mmol) in 7 N NH3 in methanol is stirred at 70° C. for 16 h in a sealed vial. The solvent is removed and the residue is purified by CC on silica gel eluting with DCM containing 7% of methanol to give 3-[4-(3-amino-propyl)-3,5-dimethyl-phenyl]-1-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propan-1-one (101 mg) as a pale yellow resin; LC-MS: tR=0.95 min, [M+1]+=412.36; 1H NMR (CDCl3): δ 6.87 (s, 2H), 3.09-3.00 (m, 4H), 2.97-2.88 (m, 4H), 2.76-2.60 (m, 6H), 2.30 (s, 2H), 2.28 (s, 6H), 1.80-1.70 (m, 2H), 1.54 (t, J=7.0 Hz, 2H), 1.26 (t, J=7.6 Hz, 3H), 0.96 (s, 6H).

Workup

  1. customThe solvent is removed
  2. customthe residue is purified by CC on silica gel eluting with DCM containing 7% of methanol

Sources & evidence

ORD record
ord-6cb7f941038345378771c3fdfc250300
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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