Potassium Carbonate → HCID 11221175, compound

HRID 917712Notes

Reaction equation

HRID 917712 reaction equation
[F:1][C:2]1[CH:22]=[C:21]([C:23]#[C:24][Si](C)(C)C)[CH:20]=[CH:19][C:3]=1[NH:4][C:5]1[C:6]([C:12]([NH:14][CH2:15][CH2:16][CH2:17][OH:18])=[O:13])=[CH:7][NH:8][C:9](=[O:11])[CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CO.C1COCC1>[C:23]([C:21]1[CH:20]=[CH:19][C:3]([NH:4][C:5]2[C:6]([C:12]([NH:14][CH2:15][CH2:16][CH2:17][OH:18])=[O:13])=[CH:7][NH:8][C:9](=[O:11])[CH:10]=2)=[C:2]([F:1])[CH:22]=1)#[CH:24]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58962862HCID 58962862, compound

Product 1

HCID 11221175HCID 11221175, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-{2-Fluoro-4-[(trimethylsilyl)ethynyl]anilino}-N-(3-hydroxypropyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide was reacted with K2CO3 in MeOH/THF as for example 12, step B. The resulting crude product was purified by column chromatography on silica gel (10% MeOH/CH2Cl2 as eluant) to give 4-(4-ethynyl-2-fluoroanilino)-N-(3-hydroxypropyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a pale yellow solid (68%), m.p. (EtOAc/MeOH) 249-252° C. 1H NMR [(CD3)2SO, 400 MHz] δ 11.42 (br s, 1H), 10.44 (s, 1H), 8.46 (s, 1H), 7.93 (s, 1H), 7.49 (t, J=8.5 Hz, 1H), 7.45 (dd, J=11.4, 1.9 Hz, 1H), 7.33 (dd, J=8.3, 1.3 Hz, 1H), 5.63 (s, 1H), 4.43 (t, J=5.2 Hz, 1H), 4.23 (s, 1H), 3.46 (q, J=5.9 Hz, 2H), 3.31-3.22 (m, 2H), 1.66 (pentet, J=6.7 Hz, 2H). Anal. Calcd for C17H16FN3O3: C, 62.0; H, 4.9; N, 12.8. Found: C, 62.0; H, 5.2; N, 12.8.

Workup

  1. customThe resulting crude product was purified by column chromatography on silica gel (10% MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-e06df6f051d84d3d8343c3022cee1262
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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