(1S)-(+)-Camphor-10-sulphonic acid → HCID 86688189, compound

HRID 1428282Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([NH:23][C:24]2[CH:25]=[C:26]([C:36]([F:39])([F:38])[F:37])[CH:27]=[C:28]([N:30]3[CH:34]=[N:33][C:32]([CH3:35])=[CH:31]3)[CH:29]=2)=[O:22])=[CH:6][C:7]=1[NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[N:19][CH:20]=2)[N:14]=1.[C@:40]12([CH2:50][S:51]([OH:54])(=[O:53])=[O:52])[C:47]([CH3:49])([CH3:48])[CH:44]([CH2:45][CH2:46]1)[CH2:43][C:41]2=[O:42]>CC(OC)(C)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([NH:23][C:24]2[CH:25]=[C:26]([C:36]([F:38])([F:39])[F:37])[CH:27]=[C:28]([N:30]3[CH:34]=[N:33][C:32]([CH3:35])=[CH:31]3)[CH:29]=2)=[O:22])=[CH:6][C:7]=1[NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[N:19][CH:20]=2)[N:14]=1.[C:40]12([CH2:50][S:51]([O-:54])(=[O:52])=[O:53])[C:47]([CH3:49])([CH3:48])[CH:44]([CH2:45][CH2:46]1)[CH2:43][C:41]2=[O:42]

Participants

Conditions

Temperature: 5 °C

Procedure

Nilotinib base (0.300 g, 0.57 mmol) was dissolved in TFE (2 mL) at 40° C. to obtain a mixture. The mixture was stirred and added to a solution of (S)-camphor-sulfonic acid (0.132 g, 0.57 mmol) in TFE (1 mL) at 40° C. The resulting clear solution was stirred for about 4 h at 40° C. and it was subsequently cooled to 5° C. The mixture was kept at 5° C. overnight and then MTBE (1.5 v/v) was added to the mixture at room temperature leading to precipitation. The precipitate was filtered and the filter cake was dried at 40° C. in a vacuum oven overnight to give Nilotinib camphorsulfonate form I.

Workup

customto obtain a mixture
stirringThe resulting clear solution was stirred for about 4 h at 40° C.
customleading to precipitation
filtrationThe precipitate was filtered
customthe filter cake was dried at 40° C. in a vacuum oven overnight

Sources & evidence

ORD record: ord-04e1161d2b93498cbde1f32e89488e52
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937082B2

Reaction notes

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