2-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid → HCID 59304368, compound

HRID 2241376Notes

Reaction equation

HRID 2241376 reaction equation
[NH2:1][C:2]1[CH:36]=[CH:35][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[N:13](CC4C=CC(OC)=CC=4)[N:14]=[C:15]([NH:16][CH:17]4[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]4)[C:8]=23)=[C:4]([F:37])[CH:3]=1.[F:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]2[C:50](=[O:51])[C:49]([C:52](O)=[O:53])=[CH:48][CH:47]=[N:46]2)=[CH:41][CH:40]=1>>[F:37][C:4]1[CH:3]=[C:2]([NH:1][C:52]([C:49]2[C:50](=[O:51])[N:45]([C:42]3[CH:43]=[CH:44][C:39]([F:38])=[CH:40][CH:41]=3)[N:46]=[CH:47][CH:48]=2)=[O:53])[CH:36]=[CH:35][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[NH:13][N:14]=[C:15]([NH:16][CH:17]3[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][OH:25])[CH2:21][CH2:22]3)[C:8]=12

Participants

3

Reactant 2

HCID 667671712-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acidHCID 68515968HCID 68515968, compound

Product 1

HCID 59304368HCID 59304368, compoundYield 55%

Procedure

Prepared by a 2-step process from 2-(4-(4-(4-amino-2-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-ylamino)piperidin-1-yl)ethanol (prepared as described in Example 101, Step A except using 2-(4-aminopiperidin-1-yl)ethanol) and 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid according to the procedure of Example 101, Step B. The crude material was rinsed with Et2O to afford 11 mg (55%) of the desired product. LRMS (ESI pos) m/e 603.1 (M+1). 1H-NMR (400 MHz, CD3OD/CDCl3) δ 8.42 (d, 1H), 8.31 (d, 1H), 8.13 (d, 1H), 8.0 (dd, 1H), 7.63 (m, 2H), 7.45 (d, 1H), 7.33 (t, 1H), 7.28 (t, 2H), 6.10 (d, 1H), 3.72 (m, 3H), 3.03 (m, 2H), 2.65 (m, 2H), 2.40 (m, 2H), 2.25 (m, 2H), 1.67 (m, 2H); 19F NMR (376 MHz, CD3OD/CDCl3) δ −112.1, −126.9.

Workup

  1. washThe crude material was rinsed with Et2O

Sources & evidence

ORD record
ord-57bb4e153e32446b9bc24c922d27f8ed
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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