6-Methylpyrimidin-4-amine → [2-(2,6-Dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine

HRID 626745Notes

Reaction equation

HRID 626745 reaction equation
ClC1C=C(C=C(Cl)C=1N1C=C2C([NH:19][C:20]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22][N:21]=3)=NC=C(Cl)C2=N1)C#N.Br[C:30]1[C:35]2=[CH:36][N:37]([C:39]3[C:44]([Cl:45])=[CH:43][C:42]([F:46])=[CH:41][C:40]=3[Cl:47])[N:38]=[C:34]2[C:33]([F:48])=[CH:32][N:31]=1.CC1N=CN=C(N)C=1>>[Cl:47][C:40]1[CH:41]=[C:42]([F:46])[CH:43]=[C:44]([Cl:45])[C:39]=1[N:37]1[CH:36]=[C:35]2[C:30]([NH:19][C:20]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22][N:21]=3)=[N:31][CH:32]=[C:33]([F:48])[C:34]2=[N:38]1

Participants

4

Reactant 3

HCID 5728526-Methylpyrimidin-4-amineHCID 696715103,5-Dichloro-4-[7-chloro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitrileHCID 866970614-Bromo-2-(2,6-dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

Product 1

HCID 89817332[2-(2,6-Dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amineYield 36%

Procedure

Following the procedure described for 3,5-dichloro-4-[7-chloro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitrile, 4-bromo-2-(2,6-dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine and 6-methylpyrimidin-4-ylamine were reacted to afford the title compound as a white solid (38 mg, 36% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.72 (s, 1H), 9.26 (d, J=2.6 Hz, 1H), 8.69 (d, J=1.2 Hz, 1H), 8.36 (s, 1H), 7.98 (d, J=3.5 Hz, 1H), 7.96 (s, 1H), 7.94 (s, 1H), 2.44 (s, 3H). LCMS (Method B): RT=3.44 min, m/z: 407 [M+H+].

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-f615482c8cb34a7dba88a83a9625b102
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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