Hydrochloric Acid → HCID 11464600, compound

HRID 917738Notes

Reaction equation

HRID 917738 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[CH:16]=[C:15]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=2[F:27])[C:14]([C:28]([NH2:30])=[O:29])=[CH:13]1)(C(C)(C)C)(C)C.Cl.[Si](O[Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C>CCO>[F:27][C:21]1[CH:22]=[C:23]([I:26])[CH:24]=[CH:25][C:20]=1[NH:19][C:15]1[C:14]([C:28]([NH2:30])=[O:29])=[CH:13][N:12]([CH2:11][CH2:10][CH2:9][OH:8])[C:17](=[O:18])[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 590018TBDMS etherHCID 23631098HCID 23631098, compound

Product 1

HCID 11464600HCID 11464600, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxamide was dissolved in EtOH and treated with 1 M HCl, as for example 22, step D, deprotecting the t-butyldimethylsilyl ether to give 4-(2-fluoro-4-iodoanilino)-1-(3-hydroxypropyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a white solid which was recrystallised from EtOAc/MeOH (86%), m.p. (EtOAc/MeOH) 220-223° C. 1H NMR [(CD3)2SO, 400 MHz] δ 10.40 (s, 1H), 8.29 (s, 1H), 7.91 (br s, 1H), 7.72 (dd, J=10.2, 1.8 Hz, 1H), 7.56 (br d, J=8.4 Hz, 1H), 7.46 (br s, 1H), 7.30 (t, J=8.5 Hz, 1H), 5.56 (s, 1H), 4.58 (t, J=5.1 Hz, 1H), 3.86 (t, J=7.2 Hz, 2H), 3.41 (q, J=5.7 Hz, 2H), 1.79 (pentet, J=6.6 Hz, 2H). Anal. Calcd for C15H15FIN3O3: C, 41.8; H, 3.5; N, 9.8. Found: C, 42.0; H, 3.4; N, 9.6.

Sources & evidence

ORD record
ord-cd1bf4bde1de44e1b6b89f6a50f4bc1b
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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