Butanal → HCID 68911840, compound

HRID 729516Notes

Reaction equation

HRID 729516 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)[CH2:33][CH2:34][CH3:35].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)[CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 3

HCID 261ButanalHCID 887MethanolHCID 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 68911840HCID 68911840, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 25 mg (0.061 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 0.011 mL (0.12 mmol) butyraldehyde and 26 mg (0.12 mmol) NaBH3(CN) before 1 mL methanol was consequently added. The mixture was stirred at ambient temperature for 15 h when MS showed that all starting materials had converted 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. MS (ES+): 468 (M+H)+.

Workup

  1. additionwas consequently added
  2. washwashed with 20 mL
  3. dry with materialNaHCO3, and dried over anhydrous Na2SO4
  4. customAfter purification by chromatography

Sources & evidence

ORD record
ord-813bd6e483f74273956666456deb450b
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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