Oxalyl chloride → N-Methyl-4-(5-methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)-N-(3-pyridinylmethyl)benzamide

HRID 931418Notes

Reaction equation

HRID 931418 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24].[CH3:33][NH:34][CH2:35][C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1>>[CH3:33][N:34]([CH2:35][C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)[C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([C:11]2[O:12][C:8]([CH3:7])=[C:9]([CH2:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[N:10]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 883933-(Methylaminomethyl)pyridineHCID 532133574-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoic Acid

Product 1

HCID 56963369N-Methyl-4-(5-methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)-N-(3-pyridinylmethyl)benzamideYield 67.7%

Procedure

Reaction of oxalyl chloride (132 λL, 1.5 mmol) and benzoic acid 4 (376 mg, 1.0 mmol) with subsequent coupling to N-methyl-N-(3-pyridinylmethyl)amine (51 mg, 1.1 mmol) gave benzamide 11 (322 mg, 67%) as a white powder: mp (EtOAc) 77-80° C.; 1H NMR δ 8.59 (br s, 1H, H-2′), 8.52 (br d, J=4.5 Hz, 1H, H-6′), 7.87 (br d, J=7.6 Hz, 2H, H-2, H-6), 7.77 (br s, 1H, H-4′), 7.66 (br d, J=8.2 Hz, 2H, H-2″, H-6″), 7.58 (br s, 2H, H-3, H-5), 7.38-7.44 (m, 3H, H-5′, H-3″, H-5″), 4.71 (br s, 2H, CH2N), 4.62 (s, 2H, CH2SO2), 2.90 (s, 3H, NCH3), 2.39 (s, 3H, CH3), 2.11 (s, 3H, CH3); 13C NMR δ 169.7, 158.0, 149.7, 149.1, 148.6, 144.5, 137.6, 135.6, 135.5, 132.9, 129.6 (2), 128.2 (2), 127.8 (2), 127.4, 125.9, 125.5 (2), 123.7, 52.9, 47.8, 37.0, 21.0, 9.6; MS m/z 476.7 (MH+, 100%). Anal. calcd for C26H25N3O4S: C, 65.67; H, 5.30; N, 8.84. Found: C, 65.46; H, 5.37; N, 8.67%.

Sources & evidence

ORD record
ord-e18645ab4bb04673890e4d83ee5cae1a
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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