(S)-5-(1-Amino-2-(dimethylamino)ethyl)-2-chlorobenzonitrile → HCID 76072990, compound

HRID 59975Notes

Reaction equation

HRID 59975 reaction equation
[NH2:1][C@@H:2]([C:7]1[CH:8]=[CH:9][C:10]([Cl:15])=[C:11]([CH:14]=1)[C:12]#[N:13])[CH2:3][N:4]([CH3:6])[CH3:5].O[C:17]1[C:18]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([NH2:29])=[O:28])[C:19]=2[N:20]=[N:21][N:22]=1>>[Cl:15][C:10]1[CH:9]=[CH:8][C:7]([C@H:2]([NH:1][C:17]2[C:18]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([NH2:29])=[O:28])[C:19]=3[N:20]=[N:21][N:22]=2)[CH2:3][N:4]([CH3:6])[CH3:5])=[CH:14][C:11]=1[C:12]#[N:13]

Participants

3

Reactant 2

HCID 90190353(S)-5-(1-Amino-2-(dimethylamino)ethyl)-2-chlorobenzonitrileHCID 1785136134-oxo-1H-1,2,3-benzotriazine-8-carboxamide

Product 1

HCID 76072990HCID 76072990, compound

Procedure

Compound 17 was prepared following general synthetic scheme 7 wherein (S)-5-(1-amino-2-(dimethylamino)ethyl)-2-chlorobenzonitrile was reacted with 4-hydroxybenzo[d][1,2,3]-triazine-8-carboxamide to give the title compound. LC-MS [397 (M+1)], 1H NMR (400 MHz, DMSO-d6): δ 9.31 (s, 1H), 8.81 (d, 1H), 8.63 (d, 1H), 8.55 (d, 1H), 8.15 (d, 1H), 8.05-8.01 (m, 2H), 7.88 (dd, 1H), 7.72 (d, 1H), 5.78 (q, 1H), 2.95-2.89 (m, 1H), 2.62-2.58 (m, 1H), 2.24 (s, 6H).

Workup

  1. customCompound 17 was prepared

Sources & evidence

ORD record
ord-4e40ee5ece9747d0b094d1eca0bd41c5
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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