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 914192Notes

Reaction equation

HRID 914192 reaction equation
[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

Participants

3

Reactant 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

Product 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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e164790783e1401cb71b73f52c9066db
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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