4-(Fluoromethyl)pyrimidin-2-amine → 3,5-Dichloro-4-[4-(4-fluoromethylpyrimidin-2-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitrile

HRID 626695Notes

Reaction equation

HRID 626695 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:18]C3C=C(C)N=C(C)N=3)=[N:15][CH:16]=[CH:17][C:12]2=[N:11]1)[C:5]#[N:6].ClC1C=C(C=C(Cl)C=1N1C=C2C(Cl)=NC=CC2=N1)C#N.[F:49][CH2:50][C:51]1[CH:56]=[CH:55][N:54]=[C:53](N)[N:52]=1>>[Cl:28][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[C:9]=1[N:10]1[CH:27]=[C:13]2[C:14]([NH:18][C:53]3[N:52]=[C:51]([CH2:50][F:49])[CH:56]=[CH:55][N:54]=3)=[N:15][CH:16]=[CH:17][C:12]2=[N:11]1)[C:5]#[N:6]

Participants

4

Reactant 3

HCID 696710844-(Fluoromethyl)pyrimidin-2-amineHCID 696715893,5-Dichloro-4-[4-(2,6-dimethylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitrileHCID 866970463,5-Dichloro-4-(4-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile

Product 1

HCID 696709913,5-Dichloro-4-[4-(4-fluoromethylpyrimidin-2-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitrileYield 5%

Procedure

Following the procedure described for 3,5-dichloro-4-[4-(2,6-dimethylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitrile, 3,5-dichloro-4-(4-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile and 4-fluoromethylpyrimidin-2-ylamine were reacted to afford the title compound as a yellow solid (6 mg, 5% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.74-9.73 (m, 1H), 8.98 (d, J=5.2 Hz, 1H), 8.53 (s, 2H), 8.07 (s, 1H), 8.05 (s, 1H), 7.62 (dd, J=7.3, 0.9 Hz, 1H), 7.55-7.52 (m, 1H), 5.78-5.75 (m, 1H), 5.66-5.63 (m, 1H). LCMS (Method B): RT=3.04 min, m/z: 414 [M+H+].

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a69b0b18d4004e2d96542cc70c991bb0
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

Loading…