2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-ethyl-benzamide → 2-[5-Chloro-2-(1,4-diethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-8-ylamino)-pyrimidin-4-ylamino]-N-ethyl-benzamide

HRID 1687340Notes

Reaction equation

HRID 1687340 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:8]=2[CH2:7][N:6]([CH2:15][CH3:16])[CH2:5][CH2:4]1)[CH3:2].Cl[C:18]1[N:23]=[C:22]([NH:24][C:25]2[CH:35]=[CH:34][CH:33]=[CH:32][C:26]=2[C:27]([NH:29][CH2:30][CH3:31])=[O:28])[C:21]([Cl:36])=[CH:20][N:19]=1>>[Cl:36][C:21]1[C:22]([NH:24][C:25]2[CH:35]=[CH:34][CH:33]=[CH:32][C:26]=2[C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[N:23][C:18]([NH:14][C:11]2[CH:12]=[CH:13][C:8]3[CH2:7][N:6]([CH2:15][CH3:16])[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[C:9]=3[CH:10]=2)=[N:19][CH:20]=1

Participants

3

Reactant 2

HCID 587485472-(2,5-Dichloro-pyrimidin-4-ylamino)-N-ethyl-benzamideHCID 672642811,4-Diethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-8-ylamine

Product 1

HCID 668301152-[5-Chloro-2-(1,4-diethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-8-ylamino)-pyrimidin-4-ylamino]-N-ethyl-benzamide

Procedure

The title compound was prepared from 1,4-Diethyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamine and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-ethyl-benzamide in an analogous manner to example 712. Product was isolated as a tan solid (0.060 g, 53%); Mp 181-186° C.; LCMS (m/e) 494 (M); 1H-NMR (DMSO, 400 MHz) δ 11.56 (s, 1H), 9.30 (s, 1H), 8.81-8.74 (m, 2H), 8.21 (s, 1H), 7.75-7.77 (d, 1H, J=8.09 Hz), 7.44-7.48 (t, 1H, J=7.83 Hz), 7.23-7.25 (d, 1H, J=8.08 Hz), 7.14-7.16 (t, 2H, J=8.09 Hz), 6.99-7.01 (d, 1H, J=8.08 Hz), 3.60 (s, 2H), 3.05-3.07 (q, 2H, J=7.07 Hz), 2.92 (m, 2H), 2.77 (m, 2H), 2.39-2.41 (q, 2H, J=7.33 Hz), 1.18-1.09 (m, 6H), 1.06-1.00 (t, 3H, J=7.08 Hz).

Sources & evidence

ORD record
ord-9ff50af6d6774682a21ce1327c37c2ed
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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