Potassium Carbonate → 6-Chloro-2-(4-chloropyridine-2-carbonyl)-3-[[(s)-2-hydroxypropionyl]amino]indole

HRID 379870ノート

反応式

HRID 379870 の反応式
C([O:4][C@@H:5]([CH3:28])[C:6]([NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:19]([C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][N:22]=1)=[O:20])=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O.C(OCC)C>[Cl:18][C:14]1[CH:13]=[C:12]2[C:17]([C:9]([NH:8][C:6](=[O:7])[C@@H:5]([OH:4])[CH3:28])=[C:10]([C:19]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][N:22]=3)=[O:20])[NH:11]2)=[CH:16][CH:15]=1

参加物

6

反応物 2

HCID 11430Potassium CarbonateHCID 543710953-[(S)-2-acetoxypropionylamino]-6-chloro-2-(4-chloropyridine-2-carbonyl)indole

生成物 1

HCID 541679946-Chloro-2-(4-chloropyridine-2-carbonyl)-3-[[(s)-2-hydroxypropionyl]amino]indole収率 74.7%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

To a suspension of 3-[(S)-2-acetoxypropionylamino]-6-chloro-2-(4-chloropyridine-2-carbonyl)indole (Example 362, 316.7 mg, 0.7536 mmol) in DMSO (10 ml) was added potassium carbonate (104.2 mg, 0.7536 mmol) in water (1 ml) at room temperature. After stirring for 30 h, the mixture was diluted with diethyl ether (200 ml), and then washed with water (50 ml×3), brine (50 ml), and dried (MgSO4). Removal of solvent gave a crystalline residue, which was recrystallized from ethyl acetate to afford 213.0 mg (74.7%) of the title compound. m.p.: 244-246° C. (recrystallized from ethyl acetate) IR(KBr)ν: 3483, 3288, 1690, 1570, 1553, 1533, 1481, 1348, 1240, 1186, 737 cm−1. 1H-NMR (DMSO-d6) δ: 12.07 (1 H, br s), 11.43 (1 H, br s), 8.82 (1 H, dd, J=5.3 and 0.5 Hz), 8.26 (1 H, d, J=9.1 Hz), 8.20 (1 H, dd, J=2.1, 0.5 Hz), 7.91 (1 H, dd, J=5.4, 2.1 Hz), 7.67 (1 H, dd, J=2.0, 0.5 Hz), 7.07 (1 H, dd, J=8.9, 2.0 Hz), 6.18 (1H, d, J=4.9 Hz), 4.23 (1 H,dd, J=6.8, 4.9 Hz), 134 (3 H, d, J=6.8 Hz).

後処理

  1. washwashed with water (50 ml×3), brine (50 ml)
  2. dry with materialdried (MgSO4)
  3. customRemoval of solvent
  4. customgave a crystalline residue, which
  5. customwas recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-a5a118ba2c504eed9140297cd1122d5d
出典データセット
uspto-grants-2001_10
特許番号
US06300363B1

反応ノート

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