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Sodium cyanoborohydride → 2-{[2-(4-{4-[4-Methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenylcarbamoyl]-benzyl}-piperazin-1-yl)-ethyl]-phenoxy-phosphinoyloxy}-propionic acid ethyl ester

HRID 272108
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HRID 272108 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=2)=[CH:4][C:3]=1[NH:24][C:25]1[N:30]=[C:29]([C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)[CH:28]=[CH:27][N:26]=1.[CH2:37]([O:39][C:40](=[O:56])[CH:41]([O:43][P:44]([CH2:53][CH:54]=O)([O:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:45])[CH3:42])[CH3:38].[BH3-]C#N.[Na+]>C(O)(=O)C.CN(C=O)C>[CH2:37]([O:39][C:40](=[O:56])[CH:41]([O:43][P:44]([CH2:53][CH2:54][N:20]1[CH2:19][CH2:18][N:17]([CH2:16][C:13]2[CH:12]=[CH:11][C:10]([C:9](=[O:23])[NH:8][C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:24][C:25]4[N:30]=[C:29]([C:31]5[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=5)[CH:28]=[CH:27][N:26]=4)[CH:4]=3)=[CH:15][CH:14]=2)[CH2:22][CH2:21]1)([O:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:45])[CH3:42])[CH3:38]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 9869737Cgp-74588HCID 724660092-[(2-Oxo-ethyl)-phenoxy-phosphinoyloxy]-propionic acid ethyl ester

생성물 1

HCID 725576762-{[2-(4-{4-[4-Methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenylcarbamoyl]-benzyl}-piperazin-1-yl)-ethyl]-phenoxy-phosphinoyloxy}-propionic acid ethyl ester수율 26.2%

시약·촉매·용매 1

HCID 21926011
acetic acid N,N-dimethylformamide
용매

실험 절차

A solution of N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-4-piperazin-1-ylmethyl-benzamide (20 mg, 0.04 mmol) and 2-[(2-oxo-ethyl)-phenoxy-phosphinoyloxy]-propionic acid ethyl ester (60 mg, 0.2 mmol) in 1% Acetic Acid/DMF (1.5 mL) solution was stirred at room temperature for 7 hours followed by an addition of NaCNBH3 (30 mg, 0.24 mmol). The resulting mixture was stirred for additional 30 min when completion of the reaction was observed by LCMS. After evaporation of solvent, the residue was taken up in CH2Cl2 and then extracted with saturated aqueous NaHCO3 The organic extracts were dried in vacuo and the residue was purified by silica gel chromatography using MeOH—CH2Cl2 (7%) to afford 8 mg (26%) of the product. 31P NMR (121.4 MHz, CDCl3) δ 27.2, 28.6; MS (m/z) 764 [M+H]+.

후처리

  1. customAfter evaporation of solvent
  2. extractionextracted with saturated aqueous NaHCO3 The organic extracts
  3. customwere dried in vacuo
  4. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-61338b7b95344b2eb3f0f59adcf050ce
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07452901B2

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