2-(4-Aminopiperidin-1-yl)ethan-1-ol → 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-N-(1-(2-hydroxyethyl)piperidin-4-yl)-5-methoxybenzamide

HRID 914192노트

반응식

HRID 914192 반응식
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[C:30]([O:31][CH3:32])=[CH:29][C:25]([C:26](O)=[O:27])=[C:24]([F:33])[CH:23]=4)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:34][CH:35]1[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][OH:43])[CH2:37][CH2:36]1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[C:30]([O:31][CH3:32])=[CH:29][C:25]([C:26]([NH:34][CH:35]5[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][OH:43])[CH2:37][CH2:36]5)=[O:27])=[C:24]([F:33])[CH:23]=4)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

3

반응물 2

HCID 157334452-(4-Aminopiperidin-1-yl)ethan-1-olHCID 252536794-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzoic acid

생성물 1

HCID 579555214-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-N-(1-(2-hydroxyethyl)piperidin-4-yl)-5-methoxybenzamide

실험 절차

The title compound was synthesized from 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzoic acid and 2-(4-aminopiperidin-1-yl)ethanol as described in the General procedure for amide bond synthesis. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40-1.86 (m, 12H) 1.88-2.10 (m, 5H) 2.33-2.42 (m, 2H) 2.84 (d, J=11.4 Hz, 2H) 3.48 (q, J=6.2 Hz, 2H) 3.73 (d, J=4.6 Hz, 1H) 4.08 (t, J=14.0 Hz, 2H) 4.37 (t, J=5.4 Hz, 1H) 4.82 (t, J=8.2 Hz, 1H) 7.18 (d, J=6.6 Hz, 1H) 7.90 (dd, J=7.7, 3.4 Hz, 1H) 8.04 (s, 1H) 8.18-8.34 (m, 2H). [M+H] calc'd for C28H36F3N7O4, 592. found 592.

후처리

  1. customas described in the General procedure for amide bond synthesis
  2. customThe final compound was purified by reverse phase HPLC
  3. customto give the free base

출처 및 근거

ORD 기록
ord-e164790783e1401cb71b73f52c9066db
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026234B2

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