1,4-Diethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-8-ylamine → 8-[5-Chloro-2-(1,4-diethyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-1,4-diethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

HRID 1687345Notes

Reaction equation

HRID 1687345 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:26]=[CH:27][C:28]3[C:34](=[O:35])[N:33]([CH2:36][CH3:37])[CH2:32][CH2:31][N:30]([CH2:38][CH3:39])[C:29]=3[CH:40]=2)[C:21]([Cl:41])=[CH:20][N:19]=1>>[Cl:41][C:21]1[C:22]([NH:24][C:25]2[CH:26]=[CH:27][C:28]3[C:34](=[O:35])[N:33]([CH2:36][CH3:37])[CH2:32][CH2:31][N:30]([CH2:38][CH3:39])[C:29]=3[CH:40]=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 866339098-(2,5-Dichloro-pyrimidin-4-ylamino)-1,4-diethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

Product 1

HCID 668303148-[5-Chloro-2-(1,4-diethyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-1,4-diethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

Procedure

The title compound was prepared from 1,4-Diethyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamine and 8-(2,5-Dichloro-pyrimidin-4-ylamino)-1,4-diethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one in an analogous manner to example 712. Product was isolated as a tan solid (0.080 g, 40%). Mp 100-106° C.; LCMS (m/e) 563 (M); 1H-NMR (DMSO, 400 MHz) δ 9.27 (s, 1H), 8.90 (s, 1H), 8.23 (s, 1H), 7.52-49 (d, 1H, J=8.59 Hz), 7.46-44 (d, 1H, J=8.33 Hz), 7.31-23 (s, 2H), 7.20-18 (d, 1H, J=7.84 Hz), 7.01-6.96 (d, 1H, J=8.34 Hz), 3.67-60 (br, 1H), 3.60-55 (q, 1H, J=6.82 Hz), 3.48-42 (t, 1H, J=5.06 Hz), 3.38-31 (s, 2H), 3.31-29 (t, 1H, J=6.57 Hz), 3.16-06 (q, 1H, J=6.82 Hz), 3.10-2.96 (m, 3H), 2.84-80 (br, 1H), 2.56-40 (br, 2H), 1.21-16 (t, 3H, J=7.07 Hz), 1.18-08 (m, 9H).

Sources & evidence

ORD record
ord-1dd89c30b93846faa067869704744d00
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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