Sodium Hydroxide → HCID 11283221, compound

HRID 917725Notes

Reaction equation

HRID 917725 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([I:31])[CH:28]=[CH:27][C:3]=1[NH:4][C:5]1[C:10]([C:11]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[O:12])=[CH:9][N:8]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[C:7](=[O:26])[CH:6]=1.[OH-].[Na+].CCOC(C)=O.CO>CCO>[F:1][C:2]1[CH:30]=[C:29]([I:31])[CH:28]=[CH:27][C:3]=1[NH:4][C:5]1[C:10]([C:11]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[O:12])=[CH:9][N:8]([CH2:18][C:19]([OH:21])=[O:20])[C:7](=[O:26])[CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21584119Ethylacetate methanolHCID 58962856HCID 58962856, compound

Product 1

HCID 11283221HCID 11283221, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl (4-(2-fluoro-4-iodoanilino)-5-{[(3-hydroxypropyl)amino]carbonyl}-2-oxo-1(2H)-pyridinyl)acetate was dissolved in EtOH and treated with 1 M NaOH, as for example 1, step C, to hydrolyse the t-butyl ester to give (4-(2-fluoro-4-iodoanilino)-5-{[(3-hydroxypropyl)amino]carbonyl}2-oxo-1(2H)-pyridinyl)acetic acid as a white solid (86%), m.p. (EtOAc/MeOH) 199-202° C. 1H NMR [(CD3)2SO, 400 MHz] δ 10.12 (s, 1H), 8.39 (t, J=5.3 Hz, 1H), 8.22 (s, 1H), 7.74 (dd, J=10.2, 1.9 Hz, 1H), 7.57 (br d, J=8.4 Hz, 1H), 7.28 (t, J=8.5 Hz, 1H), 5.54 (s, 1H), 4.53-4.42 (m, 3H), 3.45 (t, J=6.3 Hz, 2 H—by D2O exchange), 3.24 (t, J=7.0 Hz, 2 H—by D2O exchange), 1.66 (pentet, J=6.6 Hz, 2H). HRMS (FAB+) calcd C17H18FIN3O5 (MH+) 490.0275, found 490.0279.

Sources & evidence

ORD record
ord-8094598702ba45a6a404a2f5f52b590f
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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