3-Pyridinemethanamine → HCID 56963561, compound

HRID 931444Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([S:17]([CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:35]=[CH:34][C:30]([C:31]([OH:33])=O)=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])(=[O:19])=[O:18])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].[N:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][NH2:43])[CH:37]=1>>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([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:33])=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])(=[O:18])=[O:19])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

Reactant 3

HCID 310183-Pyridinemethanamine

HCID 65578Oxalyl chloride

HCID 68278296HCID 68278296, compound

Product 1

HCID 56963561HCID 56963561, compoundYield 74%

Procedure

Reaction of oxalyl chloride (92 λL, 1.06 mmol) and benzoic acid 41 (294 mg, 0.70 mmol) with subsequent coupling to 3-pyridinylmethylamine (78 λL, 0.77 mmol) gave benzamide 42 (263 mg, 74%) as a white powder: mp (EtOAc) 104-108° C.; 1H NMR δ 9.23 (t, J=5.9 Hz, 1H, CONH), 8.57 (d, J=1.6 Hz, 1H, H-2′), 8.46 (dd, J=4.7, 1.5 Hz, 1H, H-6′), 8.01 (d, J=8.5 Hz, 2H, H-2, H-6), 7.92 (d, J=8.5 Hz, 2H, H-3, H-5), 7.74 (br d, J=7.5 Hz, 1H, H-4′), 7.37 (dd, J=7.5, 4.8 Hz, 1H, H-5′), 7.33 (dd, J=8.5, 2.1 Hz, 1H, H-6″), 7.25 (d, J=2.1 Hz, 1H, H-2″), 7.14 (d, J=8.5 Hz, 1H, H-5″), 4.63 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2N), 3.84 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 2.15 (s, 3H, CH3); 13C NMR δ 165.5, 157.9, 153.1, 149.9, 148.8, 148.6, 148.0, 135.3, 135.1, 134.8, 129.7, 128.8, 128.0 (2), 126.2, 125.3 (2), 123.4, 122.2, 111.2, 110.6, 55.9, 55.7, 52.9, 40.4, 9.6; MS m/z 508.7 (MH+, 100%). Anal. calcd for C26H25N3O6S.¾CH3OH: C, 60.44, 5.31; N, 7.90. Found: C, 60.58; H, 5.17; N, 7.63%.

Sources & evidence

ORD record: ord-2846903842734d7c8b525361b9803313
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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