Methanol → HCID 68907972, compound

HRID 729517Notes

Reaction equation

HRID 729517 reaction equation
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[C:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[CH:18]=2)[N:9]=1.[F:32][C:33]([F:38])([F:37])[C:34](=O)[CH3:35].CO>C(Cl)(Cl)Cl>[F:32][C:33]([F:38])([F:37])[CH:34]([N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[C:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@H:24]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH3:25])[CH:18]=2)[N:9]=1)[CH3:35]

Participants

5

Reactant 3

HCID 887MethanolHCID 9871Methyl trifluoromethyl ketoneHCID 68905806{4-[5-(2,5-Diaza-bicyclo[2.2.1]hept-2-yl)-imidazo[1,2-c]pyrimidin-7-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine

Product 1

HCID 68907972HCID 68907972, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 40 mg (0.098 mmol) {4-[5-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-imidazo[1,2-c]pyrimidin-7-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine in 1 mL chloroform was treated with 1 mL (large excess) trifluoracetone and 62 mg (0.29 mmol) NaBH3(CN), followed by addition of 1 mL methanol. The mixture was stirred at ambient temperature for 15 h when it was quenched before complete conversion to product. The reaction mixture was diluted with 20 mL DCM, washed with 20 mL satd. NaHCO3, and dried over anhydrous Na2SO4. After purification by chromatography, the title compound was obtained as a mixture of diasteriomers (9:1 by HPLC). MS (ES+): 508 (M+H)+.

Workup

  1. customwas quenched before complete conversion to product
  2. additionThe reaction mixture was diluted with 20 mL DCM
  3. washwashed with 20 mL
  4. dry with materialNaHCO3, and dried over anhydrous Na2SO4
  5. customAfter purification by chromatography

Sources & evidence

ORD record
ord-7eea72f1ac7d43608aef1a1536d9d123
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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