2-Chloro-4-hydrazinylbenzonitrile hydrochloride → HCID 24983915, compound

HRID 505745Notes

Reaction equation

HRID 505745 reaction equation
[CH:1]1([CH:6]=[C:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[C:12]([NH:17][C:18](=[O:20])[CH3:19])[CH:11]=[CH:10][C:9]=3[C:8]2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[Cl:23][C:24]1[CH:31]=[C:30]([NH:32][NH2:33])[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]>>[Cl:23][C:24]1[CH:31]=[C:30]([N:32]2[CH:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:7]3[C:8]([C:9]4[CH:10]=[CH:11][C:12]([NH:17][C:18](=[O:20])[CH3:19])=[CH:13][C:14]=4[CH2:15][CH2:16]3)=[N:33]2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]

Participants

3

Reactant 2

HCID 221118492-Chloro-4-hydrazinylbenzonitrile hydrochlorideHCID 66722599HCID 66722599, compound

Product 1

HCID 24983915HCID 24983915, compoundYield 59%

Procedure

The title compound was prepared from N-(6-(cyclopentylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide; Preparation 36 and 2-chloro-4-hydrazinylbenzonitrile hydrochloride (Preparation 1) according to Method B (tan solid, 159 mg, 0.37 mmol, 59% yield). The title compound was largely present as (O)—N-((3RS,3aSR)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazol-7-yl)acetamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08-1.59 (m, 7H), 1.65-1.87 (m, 2H), 1.98-2.05 (m, 1H), 2.06 (s, 3H), 2.13-2.24 (m, 1H), 2.78-2.97 (m, 2H), 3.51 (ddd, J=13.56, 9.26, 4.83 Hz, 1H), 4.86 (dd, J=9.26, 5.50 Hz, 1H), 7.11 (dd, J=9.26, 1.48 Hz, 1H), 7.32 (d, J=1.88 Hz, 1H), 7.46 (dd, J=8.59, 1.88 Hz, 1H), 7.60 (s, 1H), 7.64 (d, J=8.86 Hz, 1H), 7.93 (d, J=8.59 Hz, 1H), 10.11 (s, 1H). ES-MS m/z 433 (M+H).

Sources & evidence

ORD record
ord-ea5072602890435a90ce34179c9d1f7f
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

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