Acetic Anhydride → HCID 87541472, compound

HRID 1172802Notes

Reaction equation

HRID 1172802 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[Cl:8][C:9]1[N:13]2[C:14]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([F:38])=[C:24]([CH:37]=3)[C:25]([N:27]3[CH2:33][CH2:32][CH2:31][N:30]([CH2:34][CH2:35][NH3+:36])[CH2:29][CH2:28]3)=[O:26])=[CH:15][NH:16][C:17](=[O:18])[C:12]2=[CH:11][C:10]=1[Cl:39].[CH3:40][C:41](OC(C)=O)=[O:42]>N1C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[C:41]([NH:36][CH2:35][CH2:34][NH+:30]1[CH2:31][CH2:32][CH2:33][N:27]([C:25](=[O:26])[C:24]2[CH:37]=[C:20]([CH2:19][C:14]3[N:13]4[C:9]([Cl:8])=[C:10]([Cl:39])[CH:11]=[C:12]4[C:17](=[O:18])[NH:16][CH:15]=3)[CH:21]=[CH:22][C:23]=2[F:38])[CH2:28][CH2:29]1)(=[O:42])[CH3:40]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 87540407HCID 87540407, compound

Product 1

HCID 87541472HCID 87541472, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Example 20, T1 in pyridine (0.15 M) was added Ac2O (1 eq) and the resulting mixture stirred overnight at RT. The solvent was evaporated under reduced pressure and the residue was purified at the prep RP-HPLC using H2O (+0.1% TFA) and MeCN (+0.1% TFA) as eluents (C18 column), the desired fractions were lyophilized to afford the titled compound as yellow powder. 1H NMR (300 MHz, DMSO-d6) δ: 10.97 (1H, d, J=5.6 Hz), 9.51 (1H, br. S), 8.22-8.16 (1H, m), 7.37-7.26 (3H, m), 7.20 (1H, s), 6.66-6.61 (1H, m), 4.42 (2H, s), 4.10 (1H, m), 3.63-3.14 (11H, m), 2.11 (1H, m), 1.95-1.88 (4H, m). MS (ES) C24H26Cl2FN5O3 required: 521, found: 522 (M+H)+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified at the prep RP-HPLC

Sources & evidence

ORD record
ord-233fee2b81824391b66e08995c89dc8d
Source dataset
uspto-grants-2010_11
Patent number
US07834015B2

Reaction notes

Loading…