Acetic Acid → HCID 178428331, compound

HRID 2093813Notes

Reaction equation

HRID 2093813 reaction equation
[F:1][C:2]1[C:3]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=3)[C:20]([C:30]([F:33])([F:32])[F:31])=[CH:19][N:18]=2)=[CH:4][C:5]([CH3:15])=[C:6]([CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:7]=1.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[F:1][C:2]1[CH:7]=[C:6]([C@H:8]2[CH2:13][CH2:12][C@@H:11]([N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[CH2:10][CH2:9]2)[C:5]([CH3:15])=[CH:4][C:3]=1[NH:16][C:17]1[N:22]=[C:21]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)[C:20]([C:30]([F:33])([F:32])[F:31])=[CH:19][N:18]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 58257099HCID 58257099, compound

Product 1

HCID 178428331HCID 178428331, compound

Procedure

A mixture of 4-(5-fluoro-2-methyl-4-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)cyclohexanone (30 mg, 0.065 mmol), piperidine (30 μL, 0.174 mmol) and acetic acid (75 μL, 0.13 mmol) was stirred at room temperature for 1 h. Sodium triacetoxyborohydride (27.4 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-fluoro-5-methyl-4-(cis-4-(piperidin-1-yl)cyclohexyl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine; Rf: 0.41 (Silica; MeOH/DCM 8:92); ESMS m/z 532.3 (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-0f0b339fd3c3489f9f2ab30c89f0d2bb
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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