Dichloromethane → HCID 178441944, compound

HRID 254997Notes

Reaction equation

HRID 254997 reaction equation
[CH2:1]([C:5]1[C:6](=[N:11][NH:12][C:13]2[CH:14]=NC=[CH:17][CH:18]=2)[C:7]([NH2:10])=[N:8][N:9]=1)[CH2:2][CH:3]=[CH2:4].N[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.C(CC(=O)CCC=C)#N.C(Cl)Cl>CO>[CH2:1]([C:5]1[C:6](=[N:11][NH:12][C:13]2[CH:14]=[C:20]3[C:21](=[CH:17][CH:18]=2)[N:22]=[CH:23][CH:24]=[CH:25]3)[C:7]([NH2:10])=[N:8][N:9]=1)[CH2:2][CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 100093-AminopyridineHCID 24975800HCID 24975800, compoundHCID 178441947HCID 178441947, compound

Product 1

HCID 178441944HCID 178441944, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner, 5-but-3-enyl-4-(pyridin-3-ylhydrazono)-4H-pyrazol-3-ylamine was prepared from 3-aminopyridine (113 mg, 1.2 mmole) and 1-cyano-5-hexen-2-one (123 mg, 1 mmole). The crude material was pruified by preparative TLC (CH2Cl2:MeOH=21:1) to yield 131 mg (54%) of the title compound as an orange powder. MS (m/z, ES+): 243 (M+1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6) δ 11.68 (br s, 1H), 8.89 (s, 1H), 8.46 (m, 1H), 7.96 (d, 1H), 7.46 (dd, 1H), 7.19 (brs, 2H), 5.87 (m, 1H), 5.07 (dd, 1H), 4.96 (d, 1H), 2.84 (br m, 2H), 2.46 (t, 2H).

Sources & evidence

ORD record
ord-4532cfd3dccf4f2f833a31f72449d723
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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