Methanol → HCID 68905869, compound

HRID 729521Notes

Reaction equation

HRID 729521 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.[CH:32](=O)[CH:33]([CH3:35])[CH3:34].CO>C(Cl)(Cl)Cl.C(Cl)Cl>[CH2:32]([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)[CH:33]([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 887MethanolHCID 6561IsobutyraldehydeHCID 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 68905869HCID 68905869, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 110 mg (0.26 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 2.5 mL chloroform was treated with 0.24 mL (2.6 mmol) isobutyraldehyde and 170 mg (0.78 mmol) NaBH3(CN), followed by the addition of 2.5 mL methanol. The mixture was stirred at ambient temperature for 1 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+): 468 (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-53302f1374b54ede84ba89c393f70b8d
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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