HCID 135869715, compound → HCID 135869714, compound

HRID 2263696Notes

Reaction equation

HRID 2263696 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[CH2:6][CH:7]1[C:13](=[O:14])[NH:12][C:11]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:10]=2[C:9]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[N:8]1)[CH3:2].[CH2:30](C1C=C(C=CC=1)CC1C(=O)N(C)C2C=CC(Cl)=CC=2C(C2C=CC(O)=CC=2)=N1)C.C(C1C=CC(CC2C(=O)N(C)C3C=CC(Cl)=CC=3C(C3C=CC(O)=CC=3)=N2)=CC=1)C.C(C1C=CC(CC2C(=O)NC3C=CC(Cl)=CC=3C(C3C=CC(O)=CC=3)=N2)=CC=1)C>>[Cl:19][C:17]1[CH:16]=[CH:15][C:11]2[N:12]([CH3:30])[C:13](=[O:14])[CH:7]([CH2:6][C:5]3[CH:4]=[CH:3][CH:1]=[CH:2][C:27]=3[CH2:28][CH3:29])[N:8]=[C:9]([C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)[C:10]=2[CH:18]=1

Participants

5

Reactant 4

HCID 135869715HCID 135869715, compoundHCID 135869716HCID 135869716, compoundHCID 135869717HCID 135869717, compoundHCID 135869718HCID 135869718, compound

Product 1

HCID 135869714HCID 135869714, compound

Procedure

1H NMR (300 MHz, DMSO-d6), δ 1.11 (t, 3H), 2.69 (q, 2H), 3.34 (m, 2H), 3.74 (m, 1H), 6.78 (m, 2H), 7.08-7.32 (m, 7H), 7.58 (d, 1H), 7.67 (dd, 1H), 9.98 (s, 1H). MS, m/z 419.3 [M+1]. (Z)-3-(3-Ethylbenzyl)-7-chloro-5-(4-hydroxyphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one. 1H NMR (300 MHz, DMSO-d6) δ 1.16 (t, 3H), 2.57 (q, 2H), 3.2-3.35 (m, contains signals for benzylic protons and H2O), 3.60 (t, 1H), 6.79 (d, 2H), 7.02 (dt, 1H), 7.07-7.31 (m, 7H), 7.61 (dd, 1H), 9.94 (s, 1H), 10.62 (s, 1H). MS, m/z 405.2 [M+1]. (Z)-3-(3-Ethylbenzyl)-7-chloro-5-(4-hydroxyphenyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one. 1H NMR (300 MHz, DMSO-d6) δ 1.17 (t, 3H), 2.57 (q, 2H), 3.3-3.4 (m, contains signals for benzylic protons and NMe, 5H), 3.81 (t, 1H), 6.86 (d, 2H), 7.02 (dt, 1H), 7.08-7.20 (m, 3H), 7.27 (fine d, 1H), 7.38 (d, 2H), 7.63 (d, 1H), 7.73 (dd, 1H), 9.5-11 (br s). MS, m/z 419.2 [M+1]. (Z)-3-(4-Ethylbenzyl)-7-chloro-5-(4-hydroxyphenyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one. 1H NMR (300 MHz, DMSO-d6) δ 1.14 (t, 3H), 2.58 (q, 2H), 3.36-3.41 (m, 5H), 3.95 (m, 1H), 6.90 (m, 2H), 7.10-7.42 (m, 7H), 7.66 (d, 1H), 7.83 (dd, 1H), 10.0 (br s, 1H). MS, m/z 419.3 [M+1]. (Z)-3-(4-Ethylbenzyl)-7-chloro-5-(4-hydroxyphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one.

Sources & evidence

ORD record
ord-4133b054b8ff4dae99689e76083df8ff
Source dataset
uspto-grants-2010_12
Patent number
US07851465B2

Reaction notes

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