Oxalyl chloride → N-Methyl-4-(5-methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)-N-(3-pyridinyl)benzamide

HRID 931414

反応式

HRID 931414 の反応式
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][CH:27]=1)(=[O:25])=[O:24].[CH3:33][NH:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1>>[CH3:33][N:34]([C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)[C:17](=[O:19])[C:16]1[CH:15]=[CH:14][C:13]([C:11]2[O:12][C:8]([CH3:7])=[C:9]([CH2:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:24])=[O:25])[N:10]=2)=[CH:21][CH:20]=1

参加物

4

反応物 3

HCID 65578Oxalyl chlorideHCID 140376N-Methyl-3-pyridinamineHCID 532133574-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoic Acid

生成物 1

HCID 56963290N-Methyl-4-(5-methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)-N-(3-pyridinyl)benzamide収率 73.4%

実験手順

Reaction of oxalyl chloride (100 λL, 1.1 mmol) and benzoic acid 4 (275 mg, 0.7 mmol) with subsequent coupling to N-methyl-N-(3-pyridinyl)amine (88 mg, 0.8 mmol) gave benzamide 7 (237 mg, 69%) as a white powder: mp (MeOH) 195-197° C.; 1H NMR δ 8.37 (d, J=2.4 Hz, 1H, H-2′), 8.35 (dd, J=4.7, 1.5 Hz, 1H, H-6′), 7.72 (ddd, J=8.2, 2.4, 1.5 Hz, 1H, H-4′), 7.67 (br d, J=8.5 Hz, 2H, H-2, H-6), 7.63 (br d, J=8.2 Hz, 2H, H-2″, H-6″), 7.37-7.42 (m, J=8.2 Hz, 4H, H-3, H-5, H-3″, H-5″), 7.34 (ddd, J=8.2, 4.7 Hz, 1H, H-5′), 4.58 (s, 2H, CH2SO2), 3.42 (s, 3H, NCH3), 2.34 (s, 3H, CH3), 2.06 (s, 3H, CH3); 13C NMR δ 168.8, 157.8, 149.8, 148.1, 147.3, 144.4, 140.7, 137.4, 135.5, 134.2, 129.6 (2), 129.0 (2), 128.2 (2), 127.2, 125.9, 125.0 (2), 123.8, 52.9, 37.6, 21.0, 9.6; MS m/z 462.6 (MH+, 100%). Anal. calcd for C25H23N3O4S: C, 65.06; H, 5.02; N, 9.10. Found: C, 64.90; H, 4.92; N, 8.83%.

出典と根拠

ORDレコード
ord-e8e457f9c4b84a76bca0a51e4dcc3c44
出典データセット
uspto-grants-2016_03
特許番号
US09296732B2

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