Hydrochloric Acid → HCID 86650672, compound

HRID 1969473Notes

Reaction equation

[ClH:1].[CH3:2][C:3]([NH:15][C@@H:16]1[CH2:20][C@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:31])([F:30])[F:29])[CH:22]=2)[N:18]([C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=2)[C:17]1=[O:40])([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[N:6]=1)[CH3:4].C1CCCCC1>C(OCC)(=O)C>[ClH:1].[CH3:4][C:3]([NH:15][C@@H:16]1[CH2:20][C@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:31])([F:29])[F:30])[CH:22]=2)[N:18]([C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=2)[C:17]1=[O:40])([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:12])[F:13])[N:6]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

Hydrochloride Salt formation: Add concentrated HCl (2.11 mL g, 25.5 mmol) solution to a yellow solution of 4-[(3R,5R)-3-[1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamino]-2-oxo-5-(3-trifluoromethoxy-phenyl)-pyrrolidin-1-yl]-benzonitrile (10.70 g, 19.5 mmol) in ethyl acetate at 70° C. Add slowly cyclohexane (360 mL) and heat to reflux for 30 min until precipitate forms. Cool to 50° C. and stir for 2 h., then allow to stir at room temperature. Sonicate the precipitate mixture, chill in ice-bath, and filter to give 11.7 g (102% yield, undried) of 4-[(3R,5R)-3-[1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamino]-2-oxo-5-(3-trifluoromethoxy-phenyl)-pyrrolidin-1-yl]-benzonitrile hydrochloride. LC-MS ESI m/z: 549.0 (M+H)+, Tr=2.44 min., method 2.

Workup

temperatureheat
temperatureto reflux for 30 min until precipitate forms
stirringto stir at room temperature
customSonicate the precipitate mixture
temperaturechill in ice-bath
filtrationfilter

Sources & evidence

ORD record: ord-d246436c905e4746afcfa9d052876af7
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426448B2

Reaction notes

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