3-Pyridinemethanamine → HCID 56963634, compound

HRID 931448Notes

Reaction equation

HRID 931448 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])(=[O:16])=[O:15])=[CH:10][CH:9]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][NH2:40])[CH:34]=1>>[F:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:32]=[CH:31][C:27]([C:28]([NH:40][CH2:39][C:35]4[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=4)=[O:29])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])(=[O:16])=[O:15])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 65578Oxalyl chlorideHCID 68278589HCID 68278589, compound

Product 1

HCID 56963634HCID 56963634, compoundYield 78%

Procedure

Reaction of oxalyl chloride (118 λL, 1.35 mmol) and benzoic acid 47 (337 mg, 0.90 mmol) with subsequent coupling to 3-pyridinylmethylamine (101 λL, 0.99 mmol) gave benzamide 48 (325 mg, 78%) as a white powder: mp (EtOAc) 218-220° C.; 1H NMR δ 9.22 (t, J=5.9 Hz, 1H, CONH), 8.57 (d, J=1.6 Hz, 1H, H-2′), 8.47 (dd, J=4.7, 1.4 Hz, 1H, H-6′), 8.00 (d, J=8.5 Hz, 2H, H-2, H-6), 7.83-7.91 (m, 4H, H-3, H-5, H-2″, H-6″), 7.74 (br d, J=7.8 Hz, 1H, H-4′), 7.47 (br t, J=8.8 Hz, 2H, H-3″, H-5″), 7.36 (dd, J=8.8, 4.7 Hz, 1H, H-5′), 4.73 (s, 2H, CH2SO2), 4.51 (d, J=5.9 Hz, 2H, CH2N), 2.19 (s, 3H, CH3); 13C NMR δ 165.5, 165.2 (d, J=252.7), 158.1, 150.0, 148.9, 148.1, 135.4, 135.2, 134.9, 134.8 (d, J=2.9 Hz), 131.6 (2, d, J=9.9 Hz), 128.8, 128.1 (2), 125.8, 125.4 (2), 123.5, 116.4 (2, J=22.8 Hz), 52.8, 40.5, 9.7; MS m/z 466.6 (MH+, 100%). Anal. calcd for C24H20FN3O4S: C, 61.92; H, 4.33; N, 9.03. Found: C, 62.18; H, 4.38; N, 9.14%.

Sources & evidence

ORD record
ord-23cacf13fd2f41a5aa3f1374f14159a3
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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