3-Pyridinemethanamine → 4-(4-{[(4-Chlorophenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)-N-(3-pyridinylmethyl)benzamide

HRID 931428Notes

Reaction equation

HRID 931428 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])(=[O:16])=[O:15])=[CH:10][CH:9]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][NH2:40])[CH:34]=1>>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:32]=[CH:31][C:27]([C:28]([NH:40][CH2:39][C:35]4[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=4)=[O:29])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])(=[O:16])=[O:15])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 65578Oxalyl chlorideHCID 682782794-(4-{[(4-Chlorophenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)benzoic Acid

Product 1

HCID 569634574-(4-{[(4-Chlorophenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)-N-(3-pyridinylmethyl)benzamideYield 85%

Procedure

Reaction of oxalyl chloride (60 λL, 0.69 mmol) and benzoic acid 20 (179 mg, 0.46 mmol) with subsequent coupling to 3-pyridinylmethylamine (51 λL, 0.50 mmol) gave benzamide 21 (183 mg, 85%) as a white powder: mp (EtOAc) 220-222° C.; 1H NMR δ 9.20 (t, J=5.8 Hz, 1H, CONH), 8.56 (d, J=1.6 Hz, 1H, H-2′), 8.51 (dd, J=4.7, 1.6 Hz, 1H, H-6′), 8.00 (d, J=8.6 Hz, 2H, H-2, H-6), 7.88 (d, J=8.6 Hz, 2H, H-3, H-5), 7.81 (ddd, J=8.7, 2.4, 1.9 Hz, 2H, H-2″, H-6″), 7.74 (br dt, J=7.9, 1.8 Hz, 1H, H-4′), 7.70 (ddd, J=8.7, 2.4, 1.9 Hz, 2H, H-3″, H-5″), 7.36 (dd, J=7.9, 4.7 Hz, 1H, H-5′), 4.73 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2N), 2.21 (s, 3H, CH3); 13C NMR δ 165.4, 158.0, 150.0, 148.8, 148.0, 139.0, 137.3, 135.4, 135.1, 134.8, 130.2 (2), 129.2 (2), 128.7, 128.0 (2), 125.6, 125.3 (2), 123.4, 52.7, 40.4, 9.7; MS m/z 483.3 (MH+, 100%). Anal. calcd for C24H20ClN3O4S: C, 59.81; H, 4.18; N, 8.72. Found: C, 60.12; H, 4.09; N, 8.82%.

Sources & evidence

ORD record
ord-2b55b2d679454cfb98cbe56d0ba14746
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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