Acetic Anhydride → HCID 57722806, compound

HRID 222290Notes

Reaction equation

HRID 222290 reaction equation
[OH:1][CH:2]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=2)[CH:6]=[CH:5][C:4]2[CH:19]=[CH:20][C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][C:3]1=2.[CH3:28][C:29](OC(C)=O)=[O:30]>CC(O)=O>[C:29]([O:1][CH:2]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:11]=2)[CH:6]=[CH:5][C:4]2[CH:19]=[CH:20][C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][C:3]1=2)(=[O:30])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 53309969HCID 53309969, compound

Product 1

HCID 57722806HCID 57722806, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of N-(5-hydroxy-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)methanesulfonamide (50 mg, 0.13 mmol) in AcOH (1 mL) was added Ac2O (0.5 mL). The reaction mixture was heated to 120° C. for 1 d, concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 8.83 (s, 1H); 8.11 (s, 1H); 7.18-7.63 (m, 10H); 6.75 (s, 1H); 3.03 (s, 3H); 2.23 (br s, 3H). LRMS (APCI) calc'd for (C23H21N2O4S) [M+H]+, 421.1; found 421.1.

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c741f8e2bc9e4c4bb4daf850a791b83a
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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