1,2-Dichloroethane → HCID 46832592, compound

HRID 2264368Notes

Reaction equation

HRID 2264368 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[C:17]([C:36]2[CH:48]=[C:47]([F:49])[C:39]3[N:40]=[C:41]([CH3:46])[N:42]([CH:43]([CH3:45])[CH3:44])[C:38]=3[CH:37]=2)=[N:18][C:19]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[CH:25][N:24]=2)=[N:20][CH:21]=1.[CH3:50][C:51]([CH3:53])=O.ClCCCl>C(O)(=O)C>[F:15][C:16]1[C:17]([C:36]2[CH:48]=[C:47]([F:49])[C:39]3[N:40]=[C:41]([CH3:46])[N:42]([CH:43]([CH3:45])[CH3:44])[C:38]=3[CH:37]=2)=[N:18][C:19]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:30]3[CH2:31][CH2:32][N:33]([CH:51]([CH3:53])[CH3:50])[CH2:34][CH2:35]3)=[CH:25][N:24]=2)=[N:20][CH:21]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 59376686Abemaciclib Metabolites M2

Product 1

HCID 46832592HCID 46832592, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Add sodium triacetoxyborohydride (299.9 mg) to a mixture of [5-fluoro-4-(7-fluoro-3-isopropyl-2-methyl-3H-benzoimidazol-5-yl)-pyrimidin-2-yl]-(5-piperazin-1-ylmethyl-pyridin-2-yl)-amine (130 mg), acetone (31.6 μL), 1,2-dichloroethane (9 mL) and acetic acid (16.3 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 2 M followed by silica gel column chromatography eluting with DCM/methanol-NH3 2 M (3%) to afford 115 mg of the title compound. MS (ES+): m/z=521 (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 2 M (3%)

Sources & evidence

ORD record
ord-e697f783ac0841c998682549034eab29
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

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