Chloroform → HCID 68908188, compound

HRID 729539Notes

Reaction equation

HRID 729539 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[N:20]=[C:19]([N:21]3[CH2:26][CH:25]4[CH2:27][CH:22]3[CH2:23][NH:24]4)[N:18]3[CH:28]=[CH:29][N:30]=[C:17]3[CH:16]=2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.C(O[BH-](O[C:45](=O)[CH3:46])OC(=O)C)(=O)C.[Na+].[C:49](=O)(O)[O-].[Na+]>ClCCl.CC(C)=O>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[N:20]=[C:19]([N:21]3[CH2:26][C@@H:25]4[CH2:27][C@H:22]3[CH2:23][N:24]4[CH:45]([CH3:46])[CH3:49])[N:18]3[CH:28]=[CH:29][N:30]=[C:17]3[CH:16]=2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11361492HCID 11361492, compound

Product 1

HCID 68908188HCID 68908188, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was analogously synthesized by the method described in Example 55 with the addition of one step. To a solution of benzyl-(4-[5-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)imidazo[1,2-c]pyrimidin-7-yl]pyridin-2-yl)amine (0.400 g) was added chloroform (4 mL) followed by acetone (5 mL), and sodium triacetoxy borohydride (0.600 mg) at 70° C. After 30 min, work up between dichloromethane and sodium bicarbonate followed by flash column purification afforded the title compound as an off white solid. MS (ES+): 440 (M+H)+; (ES−): 438(M−H)−.

Workup

  1. additiondescribed in Example 55 with the addition of one step
  2. customfollowed by flash column purification

Sources & evidence

ORD record
ord-1d467775dee842fc9a095aa5403c23e9
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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