Ammonium Chloride → 3-(6-Dimethylaminomethyl-2-methyl-indolizin-3-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione

HRID 402882

反応式

HRID 402882 の反応式
CC(C)([O-])C.[K+].CO[C:9](=[O:21])[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=O.[CH3:22][N:23]([CH2:25][C:26]1[CH:34]=[CH:33][C:32]2[N:28]([C:29]([CH2:36][C:37]([NH2:39])=[O:38])=[C:30]([CH3:35])[CH:31]=2)[CH:27]=1)[CH3:24].[NH4+].[Cl-]>O1CCCC1.CCOC(C)=O>[CH3:22][N:23]([CH2:25][C:26]1[CH:34]=[CH:33][C:32]2[N:28]([C:29]([C:36]3[C:37](=[O:38])[NH:39][C:9](=[O:21])[C:10]=3[C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][CH:13]=3)=[C:30]([CH3:35])[CH:31]=2)[CH:27]=1)[CH3:24]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 588944Methyl 3-indoleglyoxylateHCID 23665647Potassium tert-butoxideHCID 591920212-(6-Dimethylaminomethyl-2-methyl-indolizin-3-yl)-acetamide

生成物 1

HCID 249682373-(6-Dimethylaminomethyl-2-methyl-indolizin-3-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione収率 6.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Potassium tert-butoxide (1.0 M in THF, 0.24 ml, 0.24 mmol, 3.0 equiv) is added dropwise at room temperature under an atmosphere of argon to a solution of (1H-indol-3-yl)-oxo-acetic acid methyl ester (19.2 mg, 0.090 mmol, 1.1 equiv) and of 2-(6-dimethylaminomethyl-2-methyl-indolizin-3-yl)-acetamide (20 mg, 0.08 mmol) in anhydrous tetrahydrofuran (1.0 ml, dried over molecular sieves). The reaction mixture is stirred for 30 minutes at room temperature. It is then diluted with EtOAc and poured into a saturated aqueous NH4Cl solution. After three extractions with EtOAc, the combined organic layers are dried over Na2SO4, filtered and concentrated in vacuo. Purification of the residue via preparative HPLC affords the title compound (2 mg, 6%) as its trifluoroacetate salt. 1H NMR (400 MHz, d6-DMSO): δ=11.78 (s, 1H), 10.91 (s, 1H), 9.51 (s, 1H), 8.33 (s, 1H), 7.99 (d, J=2.9 Hz, 1H), 7.54 (s, 1H), 7.35 (d, J=8.1 Hz, 1H), 7.03 (d, J=9.1 Hz, 1H), 6.95 (dt, J=8.0/1.2 Hz, 1H), 6.61 (dd, J=9.3/1.3 Hz, 1H), 6.52 (dt, J=8.1/1.0 Hz, 1H), 6.17 (d, J=8.0 Hz, 1H), 4.13 (s, 2H), 2.67 (s, 6H), 1.93 (s, 3H). MS (ES+): 399 (M+H)+.

後処理

  1. extractionAfter three extractions with EtOAc
  2. dry with materialthe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue via preparative HPLC

出典と根拠

ORDレコード
ord-0c708c0ac9eb42728a776ade3dc5e450
出典データセット
uspto-grants-2014_06
特許番号
US08742132B2

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