Pyridine → HCID 131724793, compound

HRID 984480Notes

Reaction equation

HRID 984480 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>C(Cl)Cl>[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

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 131724794HCID 131724794, compound

Product 1

HCID 131724793HCID 131724793, compound

Reagents, catalysts & solvents 1

HCID 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. NaOHlEtOH), producing a white solid, mp 102° C. (dec.). 1H NMR (DMSO-d6, 300 MHz) δ 62.85 (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, 1. H), 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.0.25H2O: C, 53.91; H, 4.25; N, 5.03. Found: 53.91; H, 4.35; N, 5.05.

Workup

  1. customfollowed by hydrolysis under basic conditions (aq. NaOHlEtOH)
  2. customproducing a white solid, mp 102° C. (dec.)

Sources & evidence

ORD record
ord-8884778deb4a4739b137603bf733ece1
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

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