1,2-Dichloroethane → HCID 46832593, compound

HRID 2264369Notes

Reaction equation

HRID 2264369 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:2].[Na+].[CH:15]1([N:18]2[C:22]3[CH:23]=[C:24]([C:28]4[C:33]([F:34])=[CH:32][N:31]=[C:30]([NH:35][C:36]5[CH:41]=[CH:40][C:39]([CH2:42][CH:43]6[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]6)=[CH:38][N:37]=5)[N:29]=4)[CH:25]=[C:26]([F:27])[C:21]=3[N:20]=[C:19]2[CH3:49])[CH2:17][CH2:16]1.ClCCCl>C(O)(=O)C>[CH:15]1([N:18]2[C:22]3[CH:23]=[C:24]([C:28]4[C:33]([F:34])=[CH:32][N:31]=[C:30]([NH:35][C:36]5[CH:41]=[CH:40][C:39]([CH2:42][CH:43]6[CH2:48][CH2:47][N:46]([CH2:1][CH3:2])[CH2:45][CH2:44]6)=[CH:38][N:37]=5)[N:29]=4)[CH:25]=[C:26]([F:27])[C:21]=3[N:20]=[C:19]2[CH3:49])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 59376685HCID 59376685, compound

Product 1

HCID 46832593HCID 46832593, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Add sodium triacetoxyborohydride (720 mg) to a mixture of [4-(3-cyclopropyl-7-fluoro-2-methyl-3H-benzoimidazol-5-yl)-5-fluoro-pyrimidin-2-yl]-(5-piperidin-4-ylmethyl-pyridin-2-yl)-amine (110 mg), 1,2 dichloroethane (1.14 mL) and acetic acid (2709 μL). Heat at 60° C. for 1 h. Remove the solvent under vacuum. Purify by strong cation exchange cartridge (SCX) eluting with methanol and then methanol-NH3 2M followed by silica gel column chromatography eluting with DCM/methanol-NH3 2M (3%) to afford 80 mg of the title compound. MS (ES+): m/z=504 (M+H)+.

Workup

  1. customRemove the solvent under vacuum
  2. customPurify by strong cation exchange cartridge (SCX)
  3. washeluting with methanol
  4. washeluting with DCM/methanol-NH3 2M (3%)

Sources & evidence

ORD record
ord-c83bd8704f2944378e97691087e283b7
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

Loading…