Methylhydrazine → HCID 86715531, compound

HRID 2284614Notes

Reaction equation

HRID 2284614 reaction equation
[CH3:1]NN.[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[C:17]([C:18]3[CH:19]=[CH:20][C:21]4[N:22]([C:24]([C:27]5[CH:31]=[CH:30][NH:29][N:28]=5)=[CH:25][N:26]=4)[CH:23]=3)=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][C:10]=1[F:11].FC1C=CC(C2C(C3C=C4C(=CC=3)N(C(N3C5C(=CC(C6C(C7C=CC(F)=C(C)C=7)=NC=CC=6)=CC=5)C=N3)=O)N=C4)=CC=CN=2)=CC=1C>>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[C:17]([C:18]3[CH:19]=[CH:20][C:21]4[N:22]([C:24]([C:27]5[CH:31]=[CH:30][N:29]([CH3:1])[N:28]=5)=[CH:25][N:26]=4)[CH:23]=3)=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][C:10]=1[F:11]

Participants

4

Reactant 3

HCID 6061MethylhydrazineHCID 86715523HCID 86715523, compoundHCID 178505551HCID 178505551, compound

Product 1

HCID 86715531HCID 86715531, compound

Procedure

6-(2-(3-Chloro-4-fluorophenyl)pyridin-3-yl)-3-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine was prepared by the reaction of MeNHNH2 and enamine, analogous to the preparation of 6-(2-(3-Chloro-4-fluorophenyl)pyridin-3-yl)-3-(1H-pyrazol-3-yl)imidazo[1,2-a]pyridine. 1H NMR (300 MHz, DMSO-d6): δ 8.74 (dd, J=4.8, 1.6 Hz, 1H), 8.43 (dd, J=1.7, 0.9 Hz, 1H), 8.42 (s, 1H), 8.04 (dd, J=7.8, 1.6 Hz, 1H), 7.89 (dd, J=9.4, 0.8 Hz, 1H), 7.73 (dt, J=8.1, 1.1 Hz, 1H), 7.67 (d, J=2.0 Hz, 1H), 7.56 (dd, J=7.8, 4.8 Hz, 1H), 7.51 (dd, J=9.3, 1.6 Hz, 1H), 7.31-7.21 (m, 2H), 6.74 (d, J=2.0 Hz, 1H), 3.82 (s, 3H). 19F NMR (282 MHz, DMSO-d6): δ −116.76 (q, J=7.3 Hz). LCMS: rt 5.09 min (A), purity 99%, MS (m/e) 404 MH+.

Sources & evidence

ORD record
ord-5b29f23fe61b408f97fa57967ab8bacf
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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