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

HRID 1428283Notes

Reaction equation

HRID 1428283 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]>>[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

3

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 644241Nilotinib

Product 1

HCID 86688189HCID 86688189, compound

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 solution was stirred for about 2 h and it was subsequently cooled to 5° C. No precipitation was observed upon cooling. The mixture was kept at 5° C. overnight while stirring and then a sample (1 ml) was taken from the mixture and evaporated to dryness under reduced pressure at 40° C. to give amorphous Nilotinib camphorsulfonate.

Workup

  1. customto obtain a mixture
  2. stirringThe resulting solution was stirred for about 2 h
  3. customNo precipitation
  4. temperatureupon cooling
  5. stirringwhile stirring
  6. customevaporated to dryness under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-8f7e4297dbc1407eab82428ba0a59161
Source dataset
uspto-grants-2015_01
Patent number
US08937082B2

Reaction notes

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