Hydrochloric Acid → Abemaciclib Metabolites M2

HRID 2264367ノート

反応式

HRID 2264367 の反応式
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[N:17][C:18]([NH:21][C:22]3[N:27]=[C:26]([C:28]4[CH:40]=[C:39]([F:41])[C:31]5[N:32]=[C:33]([CH3:38])[N:34]([CH:35]([CH3:37])[CH3:36])[C:30]=5[CH:29]=4)[C:25]([F:42])=[CH:24][N:23]=3)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.CO.O1CCOCC1>[F:42][C:25]1[C:26]([C:28]2[CH:40]=[C:39]([F:41])[C:31]3[N:32]=[C:33]([CH3:38])[N:34]([CH:35]([CH3:37])[CH3:36])[C:30]=3[CH:29]=2)=[N:27][C:22]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([CH2:14][N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:16][N:17]=2)=[N:23][CH:24]=1

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 67427599HCID 67427599、化合物

生成物 1

HCID 59376686Abemaciclib Metabolites M2収率 96.7%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a mixture of 4-{6-[5-fluoro-4-(7-fluoro-3-isopropyl-2-methyl-3H-benzoimidazol-5-yl)-pyrimidin-2-ylamino]-pyridin-3-ylmethyl}-piperazine-1-carboxylic acid tert-butyl ester (150 mg) in DCM (10 mL) and methanol (10 mL) add hydrogen chloride 4M in dioxane (194 μL). Stir 10 min and 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 120 mg of the title compound. MS (ES+): m/z=479 (M+H)+.

後処理

  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%)

出典と根拠

ORDレコード
ord-4192ad56d6ec4fa8bd8794184532c1fa
出典データセット
uspto-grants-2010_12
特許番号
US07855211B2

反応ノート

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