Acetic Anhydride → HCID 59003157, compound

HRID 2353930Notes

Reaction equation

HRID 2353930 reaction equation
C(OC(=O)C)(=O)C.C([O-])=O.[Na+].[CH:12]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][CH:21]([N:25]([C:41](=[O:43])C)[CH2:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=2)[C:20]2[CH:44]=[CH:45][C:46]([Cl:48])=[CH:47][C:19]1=2)=[O:17])([CH3:14])[CH3:13]>C(O)=O>[CH:12]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][CH:21]([N:25]([CH2:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=2)[CH:41]=[O:43])[C:20]2[CH:44]=[CH:45][C:46]([Cl:48])=[CH:47][C:19]1=2)=[O:17])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 2723810Sodium FormateHCID 11489735HCID 11489735, compound

Product 1

HCID 59003157HCID 59003157, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Add acetic anhydride (0.22 mL, 2.34 mmol) and sodium formate (26 mg, 0.39 mmol) to a solution of 5-(3,5-Bis-trifluoromethyl-benzylamino)-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester (see example 3) (40 mg, 0.078 mmol) in formic acid (0.5 mL) and stir at room temperature for 16 h. Chromatograph the residue over silica cartridge, eluting with hexanes/ethyl acetate (5:1), to afford the title compound (27 mg, 64%). 1H NMR (DMSO-d6, 300 MHz, 100° C.) δ 1.14 (d, J=6.5 Hz, 6H), 1.63-2.05 (m, 2H), 3.43 (m, 1H), 3.63 (m, 1H), 4.56-4.61 (m, 1H), 4.70-4.72 (m, 1H), 4.77-4.89 (m, 2H) 7.09 (d, J=8.3 Hz, 1H), 7.23-7.26 (m, 2H), 7.80-7.86 (m, 3H), 8.46 (s, 1H). MS (ES+): 537 (M+H).

Workup

  1. washChromatograph the residue over silica cartridge, eluting with hexanes/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-bc2228a7bae84f87a8944aa6d496c6f3
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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