Ammonia → HCID 54365653, compound

HRID 273864Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[O:40][CH2:41][C:42]([F:45])([F:44])[F:43])[C@H:9]([CH3:30])[CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([C:20](=[O:22])[NH2:21])[CH:19]=1)[N:16]([CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=O)[CH2:15][CH2:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:46].[C-]#N.[Na+]>CO>[C:1]([O:5][C:6]([N:8]([CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[O:40][CH2:41][C:42]([F:43])([F:45])[F:44])[C@H:9]([CH3:30])[CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([C:20](=[O:22])[NH2:21])[CH:19]=1)[N:16]([CH2:23][CH2:24][CH2:25][C:26]([NH2:46])=[O:28])[CH2:15][CH2:14]2)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl (R)-(-)-4-[5-[2-[N-tert-butoxycarbonyl-2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]-7-carbamoylindolin-1-yl]butyrate (187 mg) in a saturated ammonia in methanol (2 ml) was added sodium cyanide (2 mg), and the mixture was stirred in a sealed tube at 50° C. for 71 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent to give 145 mg of (R)-(-)-4-[5-[2-[N-tert-butoxycarbonyl-2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]-7-carbamoylindolin-1-yl]butyramide as an oil.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by medium pressure liquid column chromatography on silica gel using
additiona mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent

Sources & evidence

ORD record: ord-23a9e3e6618a44b8ac28c573a3e67f65
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05387603

Reaction notes

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