[2-(4-Amino-2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine → 5-Amino-3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]benzonitrile

HRID 626774Notes

Reaction equation

HRID 626774 reaction equation
NC1C=C(Cl)C(N2C=C3C(NC4C=C(C)N=CN=4)=NC=C(F)C3=N2)=C(Cl)C=1.[Cl:28][C:29]1[C:30]([N:40]2[CH:57]=[C:43]3[C:44]([NH:49][C:50]4[CH:55]=[C:54]([CH3:56])[N:53]=[CH:52][N:51]=4)=[N:45][CH:46]=[C:47]([F:48])[C:42]3=[N:41]2)=[C:31]([CH:34]=[C:35]([N+:37]([O-])=O)[CH:36]=1)[C:32]#[N:33]>>[NH2:37][C:35]1[CH:36]=[C:29]([Cl:28])[C:30]([N:40]2[CH:57]=[C:43]3[C:44]([NH:49][C:50]4[CH:55]=[C:54]([CH3:56])[N:53]=[CH:52][N:51]=4)=[N:45][CH:46]=[C:47]([F:48])[C:42]3=[N:41]2)=[C:31]([CH:34]=1)[C:32]#[N:33]

Participants

3

Reactant 2

HCID 69671162[2-(4-Amino-2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amineHCID 696719523-Chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]-5-nitrobenzonitrile

Product 1

HCID 696748775-Amino-3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]benzonitrileYield 30%

Conditions

Temperature
70 °C

Procedure

Following the procedure described for [2-(4-amino-2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine, 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]-5-nitrobenzonitrile was heated at 70° C. for 7 h to afford the title compound as a pale yellow solid (27 mg, 30% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.68 (s, 1H), 9.26 (d, J=2.6 Hz, 1H), 8.68 (d, J=1.2 Hz, 1H), 8.37 (s, 1H), 7.97 (d, J=3.5 Hz, 1H), 7.13-7.08 (m, 2H), 6.48 (s, 2H), 2.43 (s, 3H). LCMS (Method B): RT=2.88 min, m/z: 395 [M+H+].

Sources & evidence

ORD record
ord-35cab4e893574e83b74104f4bd235dd1
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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