2-(4-Chlorophenyl)acetohydrazide → HCID 178527139, compound

HRID 1158632Notes

Reaction equation

HRID 1158632 reaction equation
[O:1]=[S:2]1(=[O:21])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:17]=[C:16]([C:18]#[N:19])[C:15]([OH:20])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([NH:32][NH2:33])=O)=[CH:25][CH:24]=1>>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][C:30]2[NH:19][C:18]([C:16]3[C:15]([OH:20])=[C:14]4[C:9]([CH:10]=[CH:11][CH:12]=[N:13]4)=[C:8]([N:3]4[CH2:4][CH2:5][CH2:6][CH2:7][S:2]4(=[O:1])=[O:21])[N:17]=3)=[N:33][N:32]=2)=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 4567342-(4-Chlorophenyl)acetohydrazideHCID 66860755HCID 66860755, compound

Product 1

HCID 178527139HCID 178527139, compound

Procedure

The title compound was prepared in a similar manner to that described in example 3 from 5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carbonitrile (75 mg, 0.24 mmol) and 2-(4-chlorophenyl)acetic hydrazide (137 mg, 0.74 mmol) to give a white solid (49 mg, 43%). 1H NMR (CDCl3/CD3OD): δ 9.06 (d, J=3.6 Hz, 1 H), 8.62 (d, J=8.4 Hz, 1 H), 7.66 (dd, J=8.4, 4.0 Hz, 1 H), 7.28-7.21 (m, 4 H), 4.15 (s, 2 H), 3.89 (m, 1 H), 3.82 (m, 1 H), 3.63 (m, 1 H), 3.31 (m, 1 H), 2.41 (m, 3 H), 1.79 (m, 1 H); MS m/z 471 (M+1).

Sources & evidence

ORD record
ord-884a735969e9465f8b7283f143d5905c
Source dataset
uspto-grants-2010_10
Patent number
US07812016B2

Reaction notes

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