2-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid → HCID 178434461, compound

HRID 2241314Notes

Reaction equation

HRID 2241314 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([C:15]([OH:17])=O)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.COC1C=CC(C[N:25]2[C:29]3=[N:30][CH:31]=[CH:32][C:33]([O:34][C:35]4[N:40]=[CH:39][C:38]([NH2:41])=[CH:37][N:36]=4)=[C:28]3[C:27]([CH3:42])=[N:26]2)=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]([C:15]([NH:41][C:38]3[CH:37]=[N:36][C:35]([O:34][C:33]4[CH:32]=[CH:31][N:30]=[C:29]5[NH:25][N:26]=[C:27]([CH3:42])[C:28]=45)=[N:40][CH:39]=3)=[O:17])=[CH:11][CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 667671712-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acidHCID 685141252-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyrimidin-5-amine

Product 1

HCID 178434461HCID 178434461, compoundYield 9%

Procedure

Prepared by 2-step process (Example 19, Step D and Example 13 Step D) from 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (0.103 g, 0.442 mmol obtained from Example 19, step C), and 2-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyrimidin-5-amine (0.04 g, 0.110 mmol). The crude material was purified by preparative TLC (1.0 mm thickness, EtOAc) to afford 2.3 mg (9%) of the desired product. LRMS M+1 (459.0) observed. 1H NMR (400 MHz, CDCl3) δ 11.88 (s, 1H), 9.04 (s, 2H), 8.51 (br s, 1H), 8.40 (m, 1H), 8.27 (m, 1H), 7.59 (m, 2H), 7.23 (m, 2H), 6.94 (m, 1H), 2.50 (s, 3H).

Workup

  1. customThe crude material was purified by preparative TLC (1.0 mm thickness, EtOAc)

Sources & evidence

ORD record
ord-1a8c4c0f04354d1098024fba3f1aac2e
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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