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1,1'-Thiocarbonyldiimidazole → tert-Butyl 8-(cyclopropylmethylene)-2-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[1,5-alpha]pyrazine-7(8H)-carboxylate

HRID 133070
ノート
印刷プレビュー

反応式

HRID 133070 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:16]=[C:10]2[CH:9]1[CH:21]([CH:23]1[CH2:25][CH2:24]1)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=S)C=1>CN(C)C1C=CN=CC=1.ClC(Cl)C>[CH:23]1([CH:21]=[C:9]2[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12][N:11]3[N:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[N:16]=[C:10]23)[CH2:25][CH2:24]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 69364591[7-N-(tert-Butoxycarbonyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazin-8-yl](cyclopropyl)methanol

生成物 1

HCID 69362860tert-Butyl 8-(cyclopropylmethylene)-2-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[1,5-alpha]pyrazine-7(8H)-carboxylate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6365
1,1-Dichloroethane
溶媒

実験手順

A solution of 100 mg (0.28 mmol) of [7-N-(tert-butoxycarbonyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro [1,2,4]triazolo[1,5-α]pyrazin-8-yl](cyclopropyl)methanol (prepared as outlined in Example 3, Step A), 52.4 mg (0.294 mmol) of 1,1-thiocarbonyldiimidazole, and 3.4 mg (0.028 mmol) of 4-(dimethylamino)pyridine in 2.0 mL of dichloroethane was stirred at reflux temperature for 17 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The aqueous phase was extracted with three portions of ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate and concentrated. Purification by preparative TLC (silica gel) gave the title compound as a clear semi-solid.

後処理

  1. temperatureat reflux temperature for 17 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  4. extractionThe aqueous phase was extracted with three portions of ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customPurification by preparative TLC (silica gel)

出典と根拠

ORDレコード
ord-ffb46fd82e0a4023b0a402c3da64673f
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07390809B2

反応ノート

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