1H-Pyrazolo[3,4-b]pyridin-5-amine → 2,6-Difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(N-methylpro-pylsulfonamido)benzamide

HRID 1943970Notes

Reaction equation

HRID 1943970 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]2[CH:3]=[N:2]1.[F:11][C:12]1[C:20]([N:21]([CH3:28])[S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23])=[CH:19][CH:18]=[C:17]([F:29])[C:13]=1[C:14]([OH:16])=[O:15].[F:30][C:31]1[C:39]([NH:40][S:41]([CH2:44][CH2:45][CH3:46])(=[O:43])=[O:42])=[CH:38][CH:37]=[C:36]([F:47])[C:32]=1[C:33]([OH:35])=[O:34]>>[F:11][C:12]1[C:20]([N:21]([CH3:28])[S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23])=[CH:19][CH:18]=[C:17]([F:29])[C:13]=1[C:14]([NH:10][C:8]1[CH:9]=[C:4]2[C:3]([O:34][CH3:33])=[N:2][NH:1][C:5]2=[N:6][CH:7]=1)=[O:15].[F:11][C:12]1[C:20]([N:21]([CH3:28])[S:22]([CH2:25][CH2:26][CH3:27])(=[O:23])=[O:24])=[CH:19][CH:18]=[C:17]([F:29])[C:13]=1[C:14]([OH:16])=[O:15].[F:30][C:31]1[C:39]([NH:40][S:41]([CH2:44][CH2:45][CH3:46])(=[O:42])=[O:43])=[CH:38][CH:37]=[C:36]([F:47])[C:32]=1[C:33]([OH:35])=[O:34]

Participants

6

Reactant 3

HCID 461929221H-Pyrazolo[3,4-b]pyridin-5-amineHCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acidHCID 670321902,6-difluoro-3-(N-methylpropylsulfonamido)benzoic acid

Product 3

HCID 442236992,6-Difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(N-methylpro-pylsulfonamido)benzamideYield 66.4%HCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acidHCID 670321902,6-difluoro-3-(N-methylpropylsulfonamido)benzoic acid

Procedure

2,6-Difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(N-methylpropylsulfonamido)benzamide (66.4% yield) was prepared according to Example 1, Step E, substituting 3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-amine for 1H-pyrazolo[3,4-b]pyridin-5-amine and 2,6-difluoro-3-(N-methylpropylsulfonamido)benzoic acid for 2,6-difluoro-3-(propylsulfonamido)benzoic acid. 2,6-Difluoro-3-(N-methylpropylsulfonamido) benzoic acid was isolated by column chromatography in 18% yield as a minor byproduct from Example C. 1H NMR (400 MHz, CDCl3) δ 9.86 (br s, 1H), 8.54 (s, 1H), 8.50 (br s, 1H), 8.64 (s, 1H), 8.10 (br s, 1H), 7.54-7.60 (q, 1H), 7.03-7.07 (t, 1H), 4.11 (s, 3H), 3.32 (s, 3H), 3.08-3.12 (t, 2H), 1.89-1.95 (m, 2H), 1.06-1.11 (t, 3H); m/z (APCI-pos) M+1=440.1.

Sources & evidence

ORD record
ord-6b5a086cb58e48fd92e62b74f4ca6b1a
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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