Acetic Acid → HCID 178428334, compound

HRID 2093816Notes

Reaction equation

HRID 2093816 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=3)[C:12]([C:22]([F:25])([F:24])[F:23])=[CH:11][N:10]=2)[C:5]([CH3:26])=[CH:4][C:3]=1[CH:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(O)(=O)C.C([BH3-])#N.[Na+]>>[CH3:26][C:5]1[CH:4]=[C:3]([C@H:27]2[CH2:32][CH2:31][C@H:30]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH2:29][CH2:28]2)[C:2]([CH3:1])=[CH:7][C:6]=1[NH:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=2)[C:12]([C:22]([F:23])([F:24])[F:25])=[CH:11][N:10]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 446211234-(2,5-dimethyl-4-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)cyclohexanone

Product 1

HCID 178428334HCID 178428334, compound

Procedure

A mixture of 4-(2,5-dimethyl-4-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)cyclohexanone (40 mg, 0.087 mmol), morpholine (15 μL, 0.174 mmol) and acetic acid (75 μL, 0.13 mmol) was stirred at room temperature for 1 h. Sodium cyanoborohydride (8.2 mg, 0.13 mmol) was added to the reaction and the reaction mixture was stirred overnight. The mixture was concentrated and purified by silica chromatography (MeOH/DCM 8:92) to afford N2-(2,5-dimethyl-4-(trans-4-morpholinocyclohexyl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine; Rf: 0.38 (Silica; MeOH/DCM 8:92); ESMS m/z 530.3 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. concentrationThe mixture was concentrated
  3. custompurified by silica chromatography (MeOH/DCM 8:92)

Sources & evidence

ORD record
ord-f0235e96b33644f2b121a074f5383a5c
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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