Methyl iodide → 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)-3-methoxy-N-(1-methylazepan-4-yl)benzamide

HRID 914068Notes

Reaction equation

HRID 914068 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:39])[C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:18]=[CH:19][C:20]4[N:26]([CH3:27])[C:25](=[O:28])[C:24]([F:30])([F:29])[CH2:23][N:22]([CH:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[C:21]=4[N:36]=3)=[C:12]([O:37][CH3:38])[CH:11]=2)[CH2:3][CH2:2]1.[CH3:40]I>>[CH:31]1([N:22]2[CH2:23][C:24]([F:30])([F:29])[C:25](=[O:28])[N:26]([CH3:27])[C:20]3[CH:19]=[N:18][C:17]([NH:16][C:13]4[CH:14]=[CH:15][C:10]([C:9]([NH:8][CH:4]5[CH2:5][CH2:6][CH2:7][N:1]([CH3:40])[CH2:2][CH2:3]5)=[O:39])=[CH:11][C:12]=4[O:37][CH3:38])=[N:36][C:21]2=3)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 25253221HCID 25253221, compound

Product 1

HCID 252532224-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methylazepan-4-yl)benzamide

Procedure

The title compound was synthesized by methylating N-(Azepan-4-yl)-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)-3-methoxybenzamide using methyl iodide. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58-1.93 (m, 17H) 2.28 (br. s., 3H) 2.33 (br. s., 1H) 3.93 (s, 3H) 4.05 (t, J=14.0 Hz, 3H) 4.75 (d, J=7.1 Hz, 1H) 7.37-7.53 (m, 2H) 7.96 (s, 1H) 8.15 (d, J=7.8 Hz, 1H) 8.26 (t, J=4.0 Hz, 2H). [M+H] calc'd for C28H37F2N7O3, 558. found 558.

Workup

  1. customThe final compound was purified by reverse phase HPLC
  2. customto give the free base

Sources & evidence

ORD record
ord-72d7c35a213543ffa91b9f38c79cf072
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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