Hydrazine hydrate (1:1) → HCID 44539339, compound

HRID 455136Notes

Reaction equation

HRID 455136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]2[N:22]=[C:21]([C:23]([NH:25][NH2:26])=[O:24])[O:20][N:19]=2)=[CH:4][CH:3]=1.ClC1C=CC(C2N=C3C=CC([F:42])=CN3C=2CC2N=C(C(OCC)=O)ON=2)=CC=1.O.NN>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([F:42])=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]2[N:22]=[C:21]([C:23]([NH:25][NH2:26])=[O:24])[O:20][N:19]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 670286833-((2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carbohydrazideHCID 67028687HCID 67028687, compound

Product 1

HCID 44539339HCID 44539339, compound

Procedure

The title compound was prepared in the same fashion as that for compound 215 from ethyl 3-((2-(4-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carboxylate and hydrazine hydrate. m/e+=387 (M+H+). 1H NMR (400 MHz, in DMSO-d6): δ 10.75 (1H, D, brs, NH), δ 8.70-8.68 (1H, D, dd, J=4.4, 2.0 Hz, ArH), δ 7.83-7.80 (2H, D, d, J=8.4 Hz, ArH), δ 7.75-7.71 (1H, D, dd, J=10.0, 5.2 Hz, ArH), δ 7.55-7.53 (2H, D, d, J=8.4 Hz, ArH), δ 7.47-7.42 (1H, D, dt, J=8.4, 2.4 Hz, ArH), δ 5.01-4.75 (2H, D, brd, NH2), δ 4.74 (2H, D, s, CH2).

Sources & evidence

ORD record
ord-23f4224ee5ca40569d9eaabc65f53774
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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