3-Pyridinemethanamine → HCID 56963559, compound

HRID 931440Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])(=[O:17])=[O:16])=[CH:11][CH:10]=1.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][NH2:41])[CH:35]=1>>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:33]=[CH:32][C:28]([C:29]([NH:41][CH2:40][C:36]4[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=4)=[O:30])=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])(=[O:16])=[O:17])=[CH:11][CH:10]=1

Participants

Reactant 3

HCID 310183-Pyridinemethanamine

HCID 65578Oxalyl chloride

HCID 68278267HCID 68278267, compound

Product 1

HCID 56963559HCID 56963559, compoundYield 51.3%

Procedure

Reaction of oxalyl chloride (76 λL, 0.88 mmol) and benzoic acid 35 (226 mg, 0.58 mmol) with subsequent coupling to 3-pyridinylmethylamine (65 λL, 0.64 mmol) gave benzamide 36 (142 mg, 51%) as a white powder: mp (MeOH/EtOAc) 189-191° C.; 1H NMR δ 9.22 (t, J=5.8 Hz, 1H, CONH), 8.57 (d, J=1.7 Hz, 1H, H-2′), 8.47 (dd, J=4.7, 1.6 Hz, 1H, H-6′), 8.00 (dd, J=8.6, 1.8 Hz, 2H, H-2, H-6), 7.91 (dd, J=8.6, 1.8 Hz, 2H, H-3, H-5), 7.74 (ddd, J=8.0, 2.1, 1.4 Hz, 1H, H-4′), 7.70 (ddd, J=8.9, 3.0, 2.0 Hz, 2H, H-2″, H-6″), 7.36 (ddd, J=7.9, 4.7, 0.7 Hz, 1H, H-5′), 7.13 (ddd, J=8.9, 3.0, 2.0 Hz, 2H, H-3″, H-5″), 4.60 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2N), 3.84 (s, 3H, OCH3), 2.13 (s, 3H, CH3); 13C NMR δ 165.5, 163.3, 157.9, 149.8, 148.9, 148.0, 135.3, 135.1, 134.8, 130.4 (2), 129.8, 128.8, 128.0 (2), 126.1, 125.3 (2), 123.4, 114.3 (2), 55.7, 53.0, 40.4, 9.6; MS m/z 477.6 (MH+, 100%). Anal. calcd for C25H23N3O5S.½CH3OH: C, 62.06; H, 5.11; N, 8.51. Found: C, 61.85; H, 4.88; N, 8.62%.

Sources & evidence

ORD record: ord-ef9255fd0bac49dba05de6165fc049e8
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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