3-Pyridinemethanamine → 4-(4-{[(4-tert-Butylphenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)-N-(3-pyridinylmethyl)benzamide
Reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])(=[O:19])=[O:18])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].[N:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][NH2:43])[CH:37]=1>>[C:7]([C:11]1[CH:12]=[CH:13][C:14]([S:17]([CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:35]=[CH:34][C:30]([C:31]([NH:43][CH2:42][C:38]4[CH:37]=[N:36][CH:41]=[CH:40][CH:39]=4)=[O:32])=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])(=[O:19])=[O:18])=[CH:15][CH:16]=1)([CH3:9])([CH3:10])[CH3:8]Participants
Procedure
Method E. Reaction of oxalyl chloride (27 λL, 0.31 mmol) and benzoic acid 23 (85 mg, 0.21 mmol) with subsequent coupling to 3-pyridinylmethylamine (23 λL, 0.23 mmol) gave benzamide 24 (49 mg, 46%) as a white powder: mp (EtOAc) 177-180° C.; 1H NMR δ 9.20 (t, J=5.8Hz, 1 H, CONH), 8.57 (d, J=1.8Hz, 1 H, H-2′), 8.46 (dd, J=4.7, 1.5Hz, 1 H, H-6′), 7.98 (br d, J=8.5Hz, 2 H, H-2, H-6), 7.86 (br d, J=8.5Hz, 2 H, H-3, H-5), 7.73 (br dt, J=7.9, 1.9Hz, 1 H, H-4′), 7.70 (br dd, J=8.6, 1.9Hz, 2 H, H-2″, H-6″), 7.63 (br dd, J=8.6, 1.9Hz, 2 H, H-3″, H-5″), 7.36 (ddd, J=7.89, 4.7, 0.6Hz, 1 H, H-5′), 4.60 (s, 2 H, CH2SO2), 4.51 (d, J=5.8Hz, 2 H, CH2N), 2.14 (s, 3 H, CH3), 1.30 us, 9 H, C(CH3)31; 13C NMR δ 165.4, 157.8, 157.0, 149.8, 148.7, 148.0, 135.4, 135.3, 135.0, 134.8, 128.7, 128.1 (2), 127.9 (2), 125.9 (2), 125.3 (2), 123.3, 52.9, 40.4, 34.8, 30.6 (3), 9.5, one resonance not observed; MS m/z 504.5 (MH+, 100%). Anal. calcd for C28H29N3O4SCH3OH: C, 65.03; H, 6.21; N, 7.84. Found: C, 65.03; H, 5.94; N, 7.99%.
Sources & evidence
- ORD record
- ord-ac9a9411b48e4485bc293a76c5835815
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085570B2
Reaction notes
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