Hydrochloric Acid → HCID 11488355, compound

HRID 917722Notes

Reaction equation

HRID 917722 reaction equation
[F:1][C:2]1[CH:31]=[C:30]([I:32])[CH:29]=[CH:28][C:3]=1[NH:4][C:5]1[C:6]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])=[O:22])=[CH:7][N:8]([CH2:12][CH2:13][O:14]C2CCCCO2)[C:9](=[O:11])[CH:10]=1.Cl.O1CCCCC1OC1CCCCO1>CCO>[F:1][C:2]1[CH:31]=[C:30]([I:32])[CH:29]=[CH:28][C:3]=1[NH:4][C:5]1[C:6]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])=[O:22])=[CH:7][N:8]([CH2:12][CH2:13][OH:14])[C:9](=[O:11])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 263182Tetrahydropyranyl etherHCID 58962868HCID 58962868, compound

Product 1

HCID 11488355HCID 11488355, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Fluoro-4-iodoanilino)-N-(3-hydroxypropyl)-6-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,6-dihydro-3-pyridinecarboxamide was dissolved in EtOH and treated with 1 M HCl, as for example 22, step D, deprotecting the tetrahydropyranyl ether to give 4-(2-fluoro-4-iodoanilino)-1-(2-hydroxyethyl)-N-(3-hydroxypropyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a white solid which was recrystallised from EtOAc/MeOH (97%), m.p. (EtOAc/MeOH) 174-176° C. 1H NMR [(CD3)2SO, 400 MHz] δ 10.18 (s, 1H), 8.43 (t, J=5.4 Hz, 1H), 8.17 (s, 1H), 7.74 (dd, J=10.2, 1.8 Hz, 1H), 7.57 (br d, J=8.4 Hz, 1H), 7.28 (t, J=8.5 Hz, 1H), 5.57 (s, 1H), 4.93 (t, J=5.4 Hz, 1H), 4.50 (t, J=5.1 Hz, 1H), 3.86 (t, J=5.6 Hz, 2H), 3.60 (q, J=5.5 Hz, 2H), 3.46 (q, J=5.7 Hz, 2H), 3.31-3.23 (m, 2H), 1.66 (pentet, J=6.7 Hz, 2H). Anal. Calcd for C17H19FIN3O4: C, 43.0; H, 4.0; N, 8.8. Found: C, 43.3; H, 3.8; N, 8.9.

Sources & evidence

ORD record
ord-f00ec68e6e2441ccbd9fee294a5ecbc8
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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