3-Pyridinemethanamine → HCID 56963633, compound

HRID 931446Notes

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][C:29]([CH3:32])=[CH:28][C:27]=1[CH3:33])(=[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][C:29]([CH3:32])=[CH:28][C:27]=1[CH3:33])(=[O:25])=[O:24]

Participants

Reactant 3

HCID 310183-Pyridinemethanamine

HCID 65578Oxalyl chloride

HCID 68278282HCID 68278282, compound

Product 1

HCID 56963633HCID 56963633, compoundYield 24%

Procedure

Reaction of oxalyl chloride (31 λL, 0.35 mmol) and benzoic acid 44 (92 mg, 0.24 mmol) with subsequent coupling to 3-pyridinylmethylamine (27 λL, 0.26 mmol) gave benzamide 45 (27 mg, 24%) as a clear gum: 1H NMR δ 9.22 (t, J=5.8 Hz, 1H, CONH), 8.57 (d, J=1.5 Hz, 1H, H-2′), 8.47 (dd, J=4.7, 1.5 Hz, 1H, H-6′), 8.00 (d, J=8.4 Hz, 2H, H-2, H-6), 7.88 (d, J=8.4 Hz, 2H, H-3, H-5), 7.74 (br d, J=7.8 Hz, 1H, H-4′), 7.57 (d, J=8.1 Hz, 1H, H-5″) 7.37 (dd, J=7.8, 4.7 Hz, 1H, H-5′), 7.27 (br s, 1H, H-3″), 7.18 (d, J=8.1 Hz, 1H, H-6″), 4.61 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2N), 2.55 (s, 3H, CH3), 2.34 (s, 3H, CH3), 2.15 (s, 3H, CH3); MS m/z 476.6 (MH+, 100%). Anal. calcd for C26H25N3O4S.½CH3CO2CH2CH3: C, 64.72; H, 5.63; N, 8.09. Found: C, 64.72; H, 5.60; N, 7.75%.

Sources & evidence

ORD record: ord-1654132ea9c3497398889a9298c27783
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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