3-Pyridinemethanamine → HCID 56963560, compound

HRID 931442Notes

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]=[C:28]([O:32][CH3:33])[CH:27]=1)(=[O:25])=[O:24].[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][NH2:41])[CH:35]=1>>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:41][CH2:40][C:36]3[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=3)=[O:19])=[CH:20][CH:21]=2)=[N:10][C:9]=1[CH2:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=1)(=[O:24])=[O:25]

Participants

Reactant 3

HCID 310183-Pyridinemethanamine

HCID 65578Oxalyl chloride

HCID 68278181HCID 68278181, compound

Product 1

HCID 56963560HCID 56963560, compoundYield 26%

Procedure

Reaction of oxalyl chloride (50 λL, 0.57 mmol) and benzoic acid 38 (146 mg, 0.38 mmol) with subsequent coupling to 3-pyridinylmethylamine (43 λL, 0.42 mmol) gave benzamide 39 (47 mg, 26%) as a white powder: mp (EtOAc) 143-145° C.; 1H NMR δ 9.23 (t, J=5.8 Hz, 1H, CONH), 8.56 (d, J=1.6 Hz, 1H, H-2′), 8.46 (dd, J=4.7, 1.4 Hz, 1H, H-6′), 8.00 (br d, J=8.5 Hz, 2H, H-2, H-6), 7.91 (br d, J=8.5 Hz, 2H, H-3, H-5), 7.74 (br d, J=7.9 Hz, 1H, H-4′), 7.53 (br dd, J=8.9, 7.6 Hz, 1H, H-5″), 7.34-7.39 (m, 2H, H-5′, H-2″), 7.25-7.29 (m, 2H, H-4″, H-6″), 4.70 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2N), 3.79 (s, 3H, OCH3), 2.17 (s, 3H, CH3); 13C NMR δ 165.5, 159.4, 158.0, 150.1, 148.9, 148.1, 139.7, 135.4, 135.2, 134.9, 130.4, 128.8, 128.1 (2), 125.9, 125.4 (2), 123.5, 120.3, 120.1, 112.8, 55.6, 52.7, 40.5, 9.7; MS m/z 478.6 (MH+, 100%). Anal. calcd for C25H23N3O5S.½CH3OH: C, 62.06, 5.11; N, 8.51. Found: C, 62.23; H, 4.90; N, 8.66%.

Sources & evidence

ORD record: ord-1733f0f1e0f547478454b817317d3b9f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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