4-Aminobenzamide → HCID 71468816, compound

HRID 240881Notes

Reaction equation

HRID 240881 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:26]([F:29])([F:28])[F:27])[O:13][N:12]=[C:11]([C:14]3[S:18][C:17]([C:19](Cl)=[O:20])=[C:16]4[CH2:22][CH2:23][CH2:24][CH2:25][C:15]=34)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH2:37])=[O:36])=[CH:33][CH:32]=1>N1C=CC=CC=1>[C:35]([C:34]1[CH:38]=[CH:39][C:31]([NH:30][C:19]([C:17]2[S:18][C:14]([C:11]3[CH2:10][C:9]([C:4]4[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=4)([C:26]([F:27])([F:29])[F:28])[O:13][N:12]=3)=[C:15]3[CH2:25][CH2:24][CH2:23][CH2:22][C:16]=23)=[O:20])=[CH:32][CH:33]=1)(=[O:36])[NH2:37]

Participants

4

Reactant 2

HCID 760794-AminobenzamideHCID 71471704HCID 71471704, compound

Product 1

HCID 71468816HCID 71468816, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Stir a mixture of 3-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carbonyl chloride (48 mg, 0.1 mmol) and 4-aminobenzamide (27 mg, 0.2 mmo) in pyridine (3 mL) at ambient temperature overnight. After removal solvent under vacuum, purify the residue by preparative HPLC to afford N-(4-carbamoylphenyl)-3-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxamide as a white solid (36 mg, 62.0%). MS (m/z): 582.1 (M+1). 1H NMR (CDCl3, 400 MHz) δ 7.84 (d, J=8.4 Hz, 2H), 7.65-7.63 (m, 3H), 7.49 (s, 2H), 7.44 (s, 1H), 6.03 (s, 1H), 5.61 (s, 1H), 4.09-4.05 (d, J=16 Hz, 1H), 3.72-3.68 (d, J=16 Hz, 1H), 3.07 (s, 2H), 2.94 (s, 2H), 1.76 (s, 4H).

Workup

  1. customAfter removal solvent under vacuum
  2. custompurify the residue by preparative HPLC

Sources & evidence

ORD record
ord-d49478c0a51645f6a1c1b4351ec9a285
Source dataset
uspto-grants-2014_02
Patent number
US08648081B2

Reaction notes

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