3-Aminopyridine → HCID 56963288, compound

HRID 1526804Notes

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](O)=[O:18])=[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][CH:27]=1)(=[O:25])=[O:24].[NH2:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1>>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:33][C:34]3[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=3)=[O:18])=[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][CH:27]=1)(=[O:24])=[O:25]

Participants

Reactant 3

HCID 100093-Aminopyridine

HCID 65578Oxalyl chloride

HCID 532133574-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoic Acid

Product 1

HCID 56963288HCID 56963288, compoundYield 59%

Procedure

Method E. Reaction of oxalyl chloride (100 λL, 1.1 mmol) and benzoic acid 4 (207 mg, 0.6 mmol) with subsequent coupling to 3-aminopyridine (58 mg, 0.6 mmol) gave benzamide 5 (148 mg, 59%) as a white powder: mp (EtOAc) 248-250° C.; 1H NMR δ 10.56 (s, 1 H, CONH), 8.94 (d, J=2.2Hz, 1 H, H-2′), 8.33 (dd, J=4.7, 1.5 Hz, 1 H, H-6′), 8.20 (ddd, J=8.3, 2.5, 1.5 Hz, 1 H, H-4′), 8.10 (br d, J=8.6 Hz, 2 H, H-2, H-6), 7.97 (br d, J=8.6 Hz, 2 H, H-3, H-5), 7.69 (br d, J=8.3Hz, 2 H, H-2″, H-6″), 7.38-7.45 (m, 3 H, H-5′, H-3″, H-5″), 4.65 (s, 2 H, CH2SO2), 2.41 (s, 3 H, CH3), 2.16 (s, 3 H, CH3); 13C NMR δ 165.0, 157.9, 150.1, 144.7 (2), 144.5, 142.1, 135.6, 135.5, 129.7 (2), 129.3, 128.6 (2), 128.3 (2), 127.4, 126.1, 125.5 (2), 123.5, 53.0, 21.1, 9.7; MS m/z 448.7 (MH+, 100%). Anal. calcd for C24H21N3O4S: C, 64.41; H, 4.73; N, 9.39. Found: C, 64.18; H, 4.74; N, 9.39%.

Sources & evidence

ORD record: ord-ac374d43b72b405684a4c954d355d6b5
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085570B2

Reaction notes

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