Triethylamine → HCID 66789992, compound

HRID 641341Notes

Reaction equation

HRID 641341 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]3[O:19][CH2:18][CH2:17][N:16]([S:20]([C:23]4[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=4[O:30][CH3:31])(=[O:22])=[O:21])[C:15]=3[CH:32]=2)=[O:10])=[CH:4][C:3]=1[C:33]#[N:34].C(N([CH2:40][CH3:41])CC)C.[C:42]([O:45][CH2:46]C)(=[O:44])C>C(O)CC>[CH2:46]([O:45][C:42](=[O:44])[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]3[O:19][CH2:18][CH2:17][N:16]([S:20]([C:23]4[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=4[O:30][CH3:31])(=[O:21])=[O:22])[C:15]=3[CH:32]=2)=[O:10])=[CH:4][C:3]=1[C:33]#[N:34])[CH2:40][CH3:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66788797HCID 66788797, compound

Product 1

HCID 66789992HCID 66789992, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo-[1,4]oxazine-6-carboxylic acid (4-bromo-3-cyano-phenyl)-amide (109 mg, 0.194 mmol), triethylamine (49 mg, 0.48 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane complex (20 mg, 25 μmol) in ethyl acetate (1.5 mL) and 1-propanol (1.5 mL) was heated at 110° C. under a carbon monoxide atmosphere for 16 h, then volatile material was removed by distillation. Chromatography of the residue (SiO2; heptane-ethyl acetate gradient, then dichloromethane/methanol 9:1) followed by trituration in dichloromethane produced 4-{[4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-2-cyano-benzoic acid propyl ester (46 mg, 42%). White solid, MS (ISP)=568.2 (M−H)−.

Workup

  1. customvolatile material was removed by distillation

Sources & evidence

ORD record
ord-5b54e9d9afc240e58d4f5292e8be9be5
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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