2-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid → HCID 67347435, compound

HRID 1676404Notes

Reaction equation

HRID 1676404 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]#[N:17])[S:15][C:8]=23)=[C:4]([F:20])[CH:3]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[C:33](=[O:34])[C:32]([C:35](O)=[O:36])=[CH:31][CH:30]=[N:29]2)=[CH:24][CH:23]=1>>[C:16]([C:14]1[S:15][C:8]2[C:9](=[N:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]2[CH:18]=[CH:19][C:2]([NH:1][C:35]([C:32]3[C:33](=[O:34])[N:28]([C:25]4[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=4)[N:29]=[CH:30][CH:31]=3)=[O:36])=[CH:3][C:4]=2[F:20])[CH:13]=1)#[N:17]

Participants

3

Reactant 2

HCID 667671712-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acidHCID 67346964HCID 67346964, compound

Product 1

HCID 67347435HCID 67347435, compoundYield 83%

Procedure

Prepared from 7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridine-2-carbonitrile and 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (Example 104, Step C) according to the procedure of Example 89. The crude was purified by silica gel flash column chromatography (5% MeOH in CH2Cl2) to afford 73 mg (83%) of the desired product. LRMS (APCI pos) m/e 502.2 (M+1). 1H-NMR (400 MHz, CDCl3) δ 11.89 (s, 1H), 8.64 (d, 1H), 8.42 (d, 1H), 8.25 (d, 1H), 8.11 (s, 1H), 7.99 (dd, 1H), 7.60 (m, 2H), 7.43 (d, 1H), 7.27 (m, 3H), 7.67 (d, 1H); 19F NMR (376 MHz, CDCl3/CD3OD) δ −111.3, −126.0.

Workup

  1. customThe crude was purified by silica gel flash column chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-b66fe7eb61de48dabe3eda34f5d557ff
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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