Pyridine → HCID 131724793, compound

HRID 1815498Notes

Reaction equation

HRID 1815498 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH:23]4[C:28]([O:30]C)=[O:29])=[O:21])=[CH:14][C:13]=3[C:32]([F:35])([F:34])[F:33])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Cl[C:37]([O:39][CH3:40])=[O:38].N1C=CC=CC=1.[OH-].[Na+].CCO>C(Cl)Cl.O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([N:22]4[CH2:27][CH2:26][N:25]([C:37]([O:39][CH3:40])=[O:38])[CH2:24][CH:23]4[C:28]([OH:30])=[O:29])=[O:21])=[CH:14][C:13]=3[C:32]([F:35])([F:33])[F:34])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 23692425Sodium hydroxide ethanolHCID 131724794HCID 131724794, compound

Product 1

HCID 131724793HCID 131724793, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by treating the compound of Example 255 with methyl chloroformate and pyridine in CH2Cl2 at room temperature, and followed by hydrolysis under basic conditions (aq. NaOH/EtOH), producing a white solid, mp 102° C. (dec.). 1H NMR (DMSO-d6, 300 MHz) δ 2.85 (m, 1H), 3.02 (m, 1H), 3.20 (m, 1H), 3.40 (m, 1H), 3.62 (s, 3H), 3.88 (m, 1H), 4.29 (s, 4H), 4.35 (m, 1H), 5.15 (m, 1H), 6.90-7.10 (m, 3H), 7.30 (d, J=15.0 Hz, 1H), 7.40 (d, J=15.0 Hz, 1H), 7.54 (d, J=15.0 Hz, 1H), 7.82 (m, 1H), 8.15 (m, 1H). MS (ESI) m/z 553 (M+H)+. Anal. calcd. for C25H23F3N2O7S.0.25 H2O: C, 53.91; H, 4.25; N, 5.03. Found: 53.91; H, 4.35; N, 5.05.

Workup

  1. customproducing a white solid, mp 102° C. (dec.)

Sources & evidence

ORD record
ord-1e10b13a9ad74e159affee71c6e109bb
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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