Ammonia → HCID 86670413, compound

HRID 1972621Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=3)[C@@H:13]([CH2:33][N:34]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[S:35]([CH3:38])(=[O:37])=[O:36])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH3:45]>CO>[NH2:45][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=3)[C@@H:13]([CH2:33][N:34]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[S:35]([CH3:38])(=[O:37])=[O:36])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A 5-mL microwave vial was charged with N-(((2R)-4-((6-chloro-3-pyridinyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-N-phenylmethanesulfonamide (0.134 g, 0.194 mmol, step 1) and 2M NH3 in MeOH (2 mL). The reaction mixture was heated in an Initiator microwave reactor (Biotage AB, Inc., Uppsala, Sweden) at 140° C. for 3 h. Then the mixture was then heated at 130° C. (thermal) for 12 h. The solvent was removed and the crude product was purified by column chromatography (25 g of silica gel, 10 to 90% EtOAc in hexanes) to afford N-(((2R)-4-((6-amino-3-pyridinyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-N-phenylmethanesulfonamide (0.0385 g) as a white solid.

Workup

temperatureThen the mixture was then heated at 130° C. (thermal) for 12 h
customThe solvent was removed
customthe crude product was purified by column chromatography (25 g of silica gel, 10 to 90% EtOAc in hexanes)

Sources & evidence

ORD record: ord-cf084b030d514e7c9a79efa4fa07bba6
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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