4-(Methylsulfonyl)aniline → HCID 54575336, compound

HRID 1519240Notes

Reaction equation

HRID 1519240 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:21]([OH:23])=O)=[N:6][CH:7]=1.[CH3:24][S:25]([C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)=[N:11][C:10]=2[C:21]([NH:32][C:31]2[CH:30]=[CH:29][C:28]([S:25]([CH3:24])(=[O:27])=[O:26])=[CH:34][CH:33]=2)=[O:23])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 796174-(Methylsulfonyl)anilineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67452761HCID 67452761, compound2×

Product 1

HCID 54575336HCID 54575336, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazole-4-carboxylic acid (intermediate A 4.1, 15 mg, 0.043 mmol), 4-(methylsulfonyl)aniline (7.32 mg, 0.043 mmol) and DIPEA (0.015 ml, 0.086 mmol) in 0.6 mL of DMF was added BOP (22.7 mg, 0.051 mmol). The reaction was stirred at room temperature for 1 h and purified by reverse phase HPLC to give 5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-N-[4-(methylsulfonyl)phenyl]-1,3-oxazole-4-carboxamide: 1H NMR (400 MHz, CDCl3) δ 9.30 (s, 1H), 8.38 (d, J=2.5 Hz, 1H), 8.08 (m, 2H), 7.94 (s, 4H), 7.61 (dd, J=8.4, 2.5 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 7.19 (m, 2H), 3.06 (s, 3H); HRMS exact mass calc for C22H15ClFN3O4S2 [M+H]+: 504.0245; observed: 504.0249.

Workup

  1. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-7a1ef9315a01468d9d86e9639be96cca
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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