1-Methyl-4-piperidone → HCID 178428773, compound

HRID 406065Notes

Reaction equation

HRID 406065 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[NH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([O:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[NH:24][C:25]2[C:26]3[C:33]([CH3:34])=[C:32]([C:35]([NH2:37])=[O:36])[S:31][C:27]=3[N:28]=[CH:29][N:30]=2)[CH2:12][CH2:11]1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[F:23][C:21]1[CH:20]=[CH:19][C:18]([NH:24][C:25]2[C:26]3[C:33]([CH3:34])=[C:32]([C:35]([NH2:37])=[O:36])[S:31][C:27]=3[N:28]=[CH:29][N:30]=2)=[C:17]([O:16][C@H:13]2[CH2:14][CH2:15][C@H:10]([NH:9][CH:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[CH2:11][CH2:12]2)[CH:22]=1

Participants

6

Reactant 3

HCID 740491-Methyl-4-piperidone2×HCID 5003444Sodium cyanoborohydride2×HCID 178428774HCID 178428774, compound

Product 1

HCID 178428773HCID 178428773, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent2×

Procedure

0.019 g 1-methyl-4-piperidone in 1.5 ml MeOH followed by 1 drop acetic acid were added to a mixture of 0.070 g 4-(2-(trans-4-aminocyclohexyloxy)-4-fluorophenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide (cpd.15.2) in 2 ml methanol. Sodium cyanoborohydride was added when the mixture was stirred at rt for 40 min. After stirring at 50° C. for 3 h further 0.010 g 1-methyl-4-piperidone and 0.010 g sodium cyanoborohydride were added and heating was continued overnight.

Workup

  1. additionwere added
  2. temperatureheating
  3. waitwas continued overnight

Sources & evidence

ORD record
ord-45aacf4676774a15833ae98013a47f7e
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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