Ethyl Bromide → HCID 25254941, compound

HRID 1880904Notes

Reaction equation

[CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:37]=[CH:36][C:26]([C:27]([NH:29][N:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)=[O:28])=[CH:25][C:24]=4[O:38][CH3:39])=[N:21][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:40](Br)[CH3:41].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:37]=[CH:36][C:26]([C:27]([NH:29][N:30]5[CH2:35][CH2:34][N:33]([CH2:40][CH3:41])[CH2:32][CH2:31]5)=[O:28])=[CH:25][C:24]=4[O:38][CH3:39])=[N:21][C:8]2=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 40 °C

Procedure

4-(9-cyclohexyl-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-(piperazin-1-yl)benzamide (108 mg, 0.2 mmols), ethyl bromide (33 mg, 0.3 mmols) and N,N-diisopropyl ethylamine (106 μL, 0.3 mmols) were mixed in a screw cap vial (5 mL) in DMF (2 mL) heated at 40° C. for 5-8 hrs, then purified to provide the title compound (76.9 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99 (t, J=7.1 Hz, 3 H) 1.14-1.89 (m, 10 H) 2.33 (q, J=6.99 Hz, 2 H) 2.48 (m, 4 H) 2.93 (t, J=4.55 Hz, 4 H) 3.31 (s, 3 H) 3.93 (s, 3 H) 4.06 (t, J=13.22 Hz, 2 H) 4.45 (m, 1 H). 7.41 (d, J=8.0 Hz, 1 H) 7.43 (s, 1 H) 7.90 (s, 1 H) 8.20 (s, 1 H) 8.26 (d, J=8.08 Hz, 1 H) 9.38 (s, 1 H) [M+H] calculated for C28H38F2N8O3, 572; found 572.

Workup

custompurified

Sources & evidence

ORD record: ord-80ecbcd622454ee8991687a9ff052919
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318727B2

Reaction notes

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