Diisopropylethylamine → Benzo[1,3]dioxole-5-carboxylic acid (7-chloro-2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide

HRID 1887838ノート

反応式

HRID 1887838 の反応式
[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]=1[C:21]1[O:22][CH:23]=[CH:24][N:25]=1.[O:26]1[C:30]2[CH:31]=[CH:32][C:33]([C:35](Cl)=[O:36])=[CH:34][C:29]=2[O:28][CH2:27]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:14][C:8]1[CH:7]=[C:6]2[C:11]([C:12](=[O:13])[C:3]([CH2:2][NH:1][C:35]([C:33]3[CH:32]=[CH:31][C:30]4[O:26][CH2:27][O:28][C:29]=4[CH:34]=3)=[O:36])=[C:4]([C:21]3[O:22][CH:23]=[CH:24][N:25]=3)[N:5]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 712083323-aminomethyl-7-chloro-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one2 回

生成物 1

HCID 71217331Benzo[1,3]dioxole-5-carboxylic acid (7-chloro-2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a 20 mL vial, 3-(aminomethyl)-7-chloro-2-(oxazol-2-yl)-1-phenylquinolin-4(1H)-one (intermediate A) (20 mg, 0.057 mmol), benzo[d][1,3]dioxole-5-carbonyl chloride (12 mg, 0.065 mmol) and N,N-(dimethylamino)pyridine (DMAP) (1.0 mg, 0.085 mmol) were combined with methylene chloride (1.5 mL) to give a brown solution. N,N-diisopropylethylamine (37 mg, 0.050 mL, 0.28 mmol) was added. The reaction mixture was stirred overnight at room temperature. In the morning, LC/MS indicated complete conversion to the desired product. The reaction mixture was diluted with 10 mL methylene chloride, then the organic solution was washed with water. The organic phase was dried over Na2SO4, filtered, then concentrated over silica gel. The silica gel-supported crude product was loaded onto a 25 gram SiliCycle column. Flash chromatography (50% ethyl acetate-hexanes ramped to 75% ethyl acetate-hexanes) afforded benzo[1,3]dioxole-5-carboxylic acid (7-chloro-2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide as a brown oil. 1H NMR (300 MHz, chloroform-d) δ ppm 8.36 (d, J=8.67 Hz, 1H) 7.50 (d, J=0.94 Hz, 1H) 7.34-7.42 (m, 4H) 7.30 (dd, J=8.67, 1.88 Hz, 1H) 7.15-7.26 (m, 6H) 7.05 (d, J=0.94 Hz, 1H) 6.77 (d, J=1.88 Hz, 1H) 6.70 (d, J=8.10 Hz, 1H) 5.91 (s, 2H) 4.37 (s, 2H). MS calcd. for C27H18ClN3O5 [(M+H)+] 499.9, obsd. 500.0.

後処理

  1. customto give a brown solution

出典と根拠

ORDレコード
ord-1dcbdf5d5e0d4bf08fdb9f98835f7f89
出典データセット
uspto-grants-2013_08
特許番号
US08501732B2

反応ノート

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