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

HRID 1526841Notes

Reaction equation

HRID 1526841 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH2:17][C:18]2[N:19]=[C:20]([C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)[S:21][CH:22]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][NH2:39])[CH:33]=1>>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH2:17][C:18]2[N:19]=[C:20]([C:23]3[CH:24]=[CH:25][C:26]([C:27]([NH:39][CH2:38][C:34]4[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=4)=[O:28])=[CH:30][CH:31]=3)[S:21][CH:22]=2)(=[O:16])=[O:15])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 65578Oxalyl chlorideHCID 682781554-(4-{[(4-Methylphenyl)sulfonyl]methyl}-1,3-thiazol-2-yl)benzoic Acid

Product 1

HCID 569636374-(4-{[(4-Methylphenyl)sulfonyl]methyl}-1,3-thiazol-2-yl)-N-(3-pyridinylmethyl)benzamideYield 68.3%

Procedure

Method E. Reaction of oxalyl chloride (70 λL, 0.8 mmol) and benzoic acid 53 (200 mg, 0.54 mmol) with subsequent reaction with 3-pyridinylmethylamine (60 λL, 0.6 mmol) gave benzamide 54 (171 mg, 68%) as a white powder: mp (EtOAc) 178-181° C.; 1H NMR δ 9.19 (t, J=5.9Hz, 1 H, CONH), 8.57 (d, J=1.6Hz, 1 H, H-2″), 8.47 (dd, J=4.8, 1.5Hz, 1 H, H-6″), 7.97 (dd, J=6.7, 1.8Hz, 2 H, H-2 , H-6), 7.81 (dd, J=6.7, 1.8Hz, 2 H, H-3, H-5), 7.74 (ddd J=8.1, 2.1, 1.6Hz, 1 H, H-4″), 7.68 (s, 1 H, H-5′), 7.65 (dd, J=8.3, 1.7Hz, 2 H, H-2″, H-6″), 7.41 (br d, J=8.3Hz, 2 H, H-3″, H-5″), 7.36 (ddd, J=8.1, 4.8, 0.7Hz, 1 H, H-5″), 4.87 (s, 2 H, CH2SO2), 4.51 (d, J=5.9Hz, 2 H, CH2N), 2.40 (s, 3 H, CH3); 13C NMR δ 165.7, 165.5, 148.9, 148.1, 145.2, 144.3, 135.9, 135.3, 135.2, 135.0, 134.9, 129.5 (2), 128.2 (2), 128.1 (2), 125.9 (2), 123.4, 122.2, 57.0, 40.5, 21.0; MS m/z 464.8 (MH+, 100%). Anal. calcd for C24H21N3O3S2: C, 62.18; H, 4.57; N, 9.06. Found: C, 62.30; H, 4.55; N, 9.10%.

Sources & evidence

ORD record
ord-3b84893355be45759e147b0575c52cbd
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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