Sodium Bicarbonate → HCID 178434452, compound

HRID 2241261Notes

Reaction equation

HRID 2241261 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][N:14]=[C:15]([CH2:16]CO)[C:8]=23)=[C:4]([F:21])[CH:3]=1.FC1C=C[C:26]([N:29]2[C:34](=[O:35])[C:33]([C:36]([OH:38])=O)=[CH:32][CH:31]=N2)=CC=1.[C:39]([O-])(O)=O.[Na+]>>[F:21][C:4]1[CH:3]=[C:2]([NH:1][C:36]([C:33]2[C:34](=[O:35])[N:29]([CH3:26])[CH:39]=[CH:31][CH:32]=2)=[O:38])[CH:20]=[CH:19][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[NH:13][N:14]=[C:15]([CH3:16])[C:8]=12

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 667671712-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acidHCID 178507758HCID 178507758, compound

Product 1

HCID 178434452HCID 178434452, compoundYield 64%

Procedure

Prepared by a 2-step process from 2-(4-(4-amino-2-fluorophenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)ethanol and 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (prepared as in Example 19, Step C) according to the procedure described for Example 21, Steps A and B, except that the crude was treated with aqueous NaHCO3 solution. The crude was purified by silica gel flash column chromatography (4% MeOH in CH2Cl2) to afford 6.6 mg (64%) of the desired product. LRMS (ESI pos) m/e 505.2 (M+1). 1H NMR (400 MHz, CDCl3/CD3OD) δ 8.41 (d, 1H), 8.32 (d, 1H), 8.25 (d, 1H), 8.0 (dd, 1H), 7.64 (m, 2H), 7.46 (m, 1H), 7.33 (t, 1H), 7.28 (m, 2H), 6.26 (d, 1H), 4.06 (t, 2H), 3.38 (t, 2H); 19F NMR (376 MHz, CDCl3/CD3OD) δ −112.4, −127.5.

Workup

  1. customThe crude was purified by silica gel flash column chromatography (4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-dac876ff63e94a3fb1d3db91536d8021
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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