Methanol → HCID 68911523, compound

HRID 729518Notes

Reaction equation

HRID 729518 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.[C:32]1(=O)[CH2:36][CH2:35][CH2:34][CH2:33]1.CO>C(Cl)(Cl)Cl.C(Cl)Cl>[CH:32]1([N:5]2[CH2:6][C@@H:1]3[CH2:7][C@H:4]2[CH2:3][N:2]3[C:8]2[N:13]3[CH:14]=[CH:15][N:16]=[C:12]3[CH:11]=[C:10]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@H:24]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH3:25])[CH:18]=3)[N:9]=2)[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

6

Reactant 3

HCID 887MethanolHCID 8452CyclopentanoneHCID 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 68911523HCID 68911523, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 120 mg (0.28 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 3 mL chloroform was treated with 0.25 mL (2.8 mmol) cyclopentanone and 180 mg (0.84 mmol) NaBH3(CN), followed by addition of 5 mL methanol. The mixture was stirred at ambient temperature for 3 h when MS showed that all starting materials had converted to product. The reaction mixture was diluted with 50 mL DCM, washed with 50 mL satd. NaHCO3, and dried over anhydrous Na2SO4. After purification by HPLC, the title compound was obtained. MS (ES+): 480 (M+H)+.

Workup

  1. washwashed with 50 mL
  2. dry with materialNaHCO3, and dried over anhydrous Na2SO4
  3. customAfter purification by HPLC

Sources & evidence

ORD record
ord-b393fbad538f41758ad60b08f0c86ac9
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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