Ammonia → HCID 68592703, compound

HRID 736955Notes

Reaction equation

Cl[Si](C)(C)C.[NH2:6][C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([CH2:17][C@@H:18]([O:34]CC2C=CC=CC=2)[C:19]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)[CH2:23][CH2:22]2)=[O:20])=[CH:9][C:8]=1[Cl:42].[Na+].[I-].N>C(#N)C.C(O)(C)C.CCO>[NH2:6][C:7]1[C:12]([C:13]([F:14])([F:15])[F:16])=[CH:11][C:10]([CH2:17][C@@H:18]([OH:34])[C:19]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]3[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]3)[CH2:23][CH2:22]2)=[O:20])=[CH:9][C:8]=1[Cl:42]

Participants

Conditions

Temperature: 80 °C

Procedure

0.32 mL (2.5 mmol) chloro-trimethyl-silane were added to a suspension of 450 mg (0.84 mmol) (R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-benzyloxy-1-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-propan-1-one and 380 mg (2.5 mmol) NaI in 30 mL acetonitrile and the reaction mixture was stirred for 7 h at 80° C. 30 mL EtOH and 20 mL isopropanol were added, the mixture was stirred for 30 min at RT, 15 mL of NH3 solution were added and the mixture was stirred for a further 30 min. It was evaporated down i. vac., the residue was combined with 100 mL 15% K2CO3 solution, extracted with 100 mL EtOAc, the organic phase was separated off, washed with 3% Na2SO3 solution and trocknete over Na2SO4. After the desiccant and solvent had been eliminated the residue was further reacted without purification.

Workup

stirringthe mixture was stirred for 30 min at RT
stirringthe mixture was stirred for a further 30 min
customIt was evaporated down i
extractionextracted with 100 mL EtOAc
customthe organic phase was separated off
washwashed with 3% Na2SO3 solution and trocknete over Na2SO4
customwas further reacted without purification

Sources & evidence

ORD record: ord-4a48d13be23f4566a4eea840dfadfeb1
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595312B2

Reaction notes

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