6-Methylpyrimidin-4-amine → 3,5-Dichloro-4-[7-fluoro-4-(6-methyl-pyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]-benzonitrile

HRID 626720Notes

Reaction equation

HRID 626720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:28])[C:9]=1[N:10]1[CH:27]=[C:13]2[C:14]([NH:19][C:20]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22][N:21]=3)=[N:15][CH:16]=[C:17](Cl)[C:12]2=[N:11]1)[C:5]#[N:6].ClC1C=C(C=C(Cl)C=1N1C=C2C(Cl)=NC=C([F:46])C2=N1)C#N.CC1N=CN=C(N)C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:28])[C:9]=1[N:10]1[CH:27]=[C:13]2[C:14]([NH:19][C:20]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22][N:21]=3)=[N:15][CH:16]=[C:17]([F:46])[C:12]2=[N:11]1)[C:5]#[N:6]

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 866970553,5-Dichloro-4-(4-chloro-7-fluoro-pyrazolo[4,3-c]pyridin-2-yl)-benzonitrile

Product 1

HCID 866970543,5-Dichloro-4-[7-fluoro-4-(6-methyl-pyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]-benzonitrileYield 41%

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, 3,5-dichloro-4-(4-chloro-7-fluoro-pyrazolo[4,3-c]pyridin-2-yl)-benzonitrile and 6-methylpyrimidin-4-ylamine were reacted to afford the title compound as a white solid (35 mg, 41% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.79 (s, 1H), 9.33 (d, J=2.6 Hz, 1H), 8.69 (d, J=1.2 Hz, 1H), 8.51 (s, 2H), 8.34 (s, 1H), 8.00 (d, J=3.5 Hz, 1H), 2.44 (s, 3H). LCMS (Method B): RT=3.39 min, m/z: 416 [M+H+].

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-07a146cf14c94f77a0fa4148c09f4abd
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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