1,4-Diethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-8-ylamine → HCID 131729578, compound

HRID 1041036Notes

Reaction equation

HRID 1041036 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:39]=[CH:38][C:28]3[CH2:29][N:30]([CH2:36][CH3:37])[CH2:31][CH2:32][N:33]([CH2:34][CH3:35])[C:27]=3[CH:26]=2)[C:21]([Cl:40])=[CH:20][N:19]=1>>[Cl:40][C:21]1[C:22]([NH:24][C:25]2[CH:39]=[CH:38][C:28]3[CH2:29][N:30]([CH2:36][CH3:37])[CH2:31][CH2:32][N:33]([CH2:34][CH3:35])[C:27]=3[CH:26]=2)=[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 672642811,4-Diethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-8-ylamineHCID 86633908HCID 86633908, compound

Product 1

HCID 131729578HCID 131729578, compound

Procedure

The title compound was prepared from 1,4-Diethyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamine and (2,5-Dichloro-pyrimidin-4-yl)-(1,4-diethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-8-yl)-amine in an analogous manner to example 712. Product was isolated as a tan solid (0.025 g, 16%). Mp 75-78° C.; LCMS (m/e) 549 (M); 1H-NMR (DMSO, 400 MHz) δ 9.12 (s, 1H), 8.67 (s, 1H), 8.09 (s, 1H), 7.25-7.19 (m, 4H), 7.04 (d, 2H, J=6.82 Hz), 6.90-6.83 (d, 1H, J=7.83 Hz), 3.63 (s, 2H), 3.56 (s, 2H), 3.09-3.00 (q, 2H, J=6.32 Hz), 2.92-2.83 (m, 4H), 2.80-2.70 (m, 3H), 2.47-2.31 (m, 4H), 1.09-1.02 (m, 12H).

Sources & evidence

ORD record
ord-6810112e9ae2498ea290c911a95a43a3
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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