3-Pyridinemethanamine → 4-{4-[(Benzenesulfonyl)methyl]-5-methyl-1,3-oxazol-2-YL}-N-[(pyridin-3-YL)methyl]benzamide
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]([OH:19])=O)=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24].[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][NH2:39])[CH:33]=1>>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:39][CH2:38][C:34]3[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=3)=[O:19])=[CH:20][CH:21]=2)=[N:10][C:9]=1[CH2:22][S:23]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:25])=[O:24]Participants
Procedure
Reaction of oxalyl chloride (102 λL, 1.17 mmol) and benzoic acid 17 (280 mg, 0.78 mmol) with subsequent coupling to 3-pyridinylmethylamine (87 λL, 0.86 mmol) gave benzamide 18 (169 mg, 48%) as a white powder: mp (EtOAc) 196-198° C.; 1H NMR δ 9.20 (t, J=5.9 Hz, 1H, CONH), 8.57 (br s, 1H, H-2′), 8.46 (br s, 1H, H-6′), 8.00 (br dd, J=8.6, 1.8 Hz, 2H, H-2, H-6), 7.89 (br dd, J=8.6, 1.8 Hz, 2H, H-3, H-5), 7.80 (br d, J=8.5 Hz, 2H, H-2″, H-6″), 7.71-7.76 (m, 2H, H-4′, H-4″), 7.62 (br dd, J=8.2, 7.5 Hz, 2H, H-3″, H-5″), 7.36 (dd, J=7.8, 4.8 Hz, 1H, H-5′), 4.68 (s, 2H, CH2SO2), 4.50 (d, J=5.8 Hz, 2H, CH2N), 2.13 (s, 3H, CH3); 13C NMR δ 165.4, 157.9, 149.9, 148.8, 148.0, 138.3, 135.3, 135.0, 134.8, 133.8, 129.1 (2), 128.7, 128.1 (2), 128.0 (2), 125.8, 125.3 (2), 123.4, 52.7, 40.4, 9.5; MS m/z 448.5 (MH+, 100%). Anal. calcd for C24H21N3O4S: C, 64.41; H, 4.73; N, 9.39. Found: C, 64.23; H, 4.71; N, 9.37%.
Sources & evidence
- ORD record
- ord-92b931b3ea9b4459bb184e5ba00aa143
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296732B2
Reaction notes
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