Ammonia → 2-amino-N-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-N-methyl-acetamide

HRID 1755049Notes

Reaction equation

[NH3:1].Cl[CH2:3][C:4]([N:6]([C:8]1[CH:13]=[C:12]([CH3:14])[C:11](/[CH:15]=[CH:16]/[S:17]([N:20]2[CH2:41][CH2:40][C:23]3([N:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([F:38])([F:37])[F:36])[CH:29]=4)[NH:25][C:24]3=[O:39])[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[C:10]([CH3:42])[CH:9]=1)[CH3:7])=[O:5]>C(O)C>[NH2:1][CH2:3][C:4]([N:6]([C:8]1[CH:13]=[C:12]([CH3:14])[C:11](/[CH:15]=[CH:16]/[S:17]([N:20]2[CH2:41][CH2:40][C:23]3([N:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([F:38])([F:37])[F:36])[CH:29]=4)[NH:25][C:24]3=[O:39])[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[C:10]([CH3:42])[CH:9]=1)[CH3:7])=[O:5]

Participants

Conditions

Temperature: 55 °C

Procedure

Ammonia (6 N solution in ethanol, 0.3 ml) was added to a solution of 2-chloro-N-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-N-methyl-acetamide (38 mg, 0.06 mmol) in anhydrous ethanol (0.5 ml), and the mixture was stirred at 50 to 60° C. for five hours. The mixed solution was concentrated under reduced pressure, and the resulting residue was then purified by silica gel column chromatography (dichloromethane) to give 2-amino-N-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-N-methyl-acetamide (11 mg, 31%).

Workup

concentrationThe mixed solution was concentrated under reduced pressure
customthe resulting residue was then purified by silica gel column chromatography (dichloromethane)

Sources & evidence

ORD record: ord-36d4c33c6b864c0a82c217104c751caa
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169254B2

Reaction notes

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