Sodium Chloride → Cyclopentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

HRID 29095

反応式

HRID 29095 の反応式
Cl(O)(=O)(=O)=O.[C:6]1([C:12]#[C:13][C:14]2[S:18][C:17]([CH:19]=O)=[CH:16][CH:15]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:21]1([N+:26]#[C-:27])[CH2:25][CH2:24][CH2:23][CH2:22]1.[NH2:28][C:29]1[CH:34]=[N:33][CH:32]=[CH:31][N:30]=1.[Na+].[Cl-]>CO.C(Cl)Cl>[CH:21]1([NH:26][C:27]2[N:30]3[CH:31]=[CH:32][N:33]=[CH:34][C:29]3=[N:28][C:19]=2[C:17]2[S:18][C:14]([C:13]#[C:12][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:15][CH:16]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

8

反応物 5

HCID 5234Sodium ChlorideHCID 24247Perchloric AcidHCID 78747AminopyrazineHCID 2734784Cyclopentyl IsocyanideHCID 27371405-(Phenylethynyl)thiophene-2-carbaldehyde

生成物 1

HCID 11710726Cyclopentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine収率 47%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒3 回HCID 6344Dichloromethane溶媒

実験手順

10 μl (0.022 mmol) of 20% aq. perchloric acid, a solution of 31.8 mg (0.15 mmol) of 5-phenylethynyl-thiophene-2-carbaldehyde in a mixture of MeOH and DCM (0.5 ml, 1:1 vol/vol) and a solution of 11.1 mg (0.115 mmol) of cyclopentyl isocyanide in MeOH (0.5 ml) were added in succession to a solution of 9.5 mg (0.1 mmol) of 2-aminopyrazine in MeOH (1 ml). The reaction solution was stirred at RT for 36 h and then combined with sat. aq. NaCl solution (3 ml) and stirred at RT for a further 45 min. The phases were separated and the aq. phase was extracted with DCM (2×3 ml). The collected organic phases were dried over MgSO4, filtered and evaporated under a vacuum. The group was purified by means of preparative HPLC, wherein 18 mg (0.047 mmol, 47%) of cyclopentyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained.

後処理

  1. stirringstirred at RT for a further 45 min
  2. customThe phases were separated
  3. extractionthe aq. phase was extracted with DCM (2×3 ml)
  4. dry with materialThe collected organic phases were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under a vacuum
  7. customThe group was purified by means of preparative HPLC

出典と根拠

ORDレコード
ord-d87eaf0a58864e0d80a02fd7c00519b7
出典データセット
uspto-grants-2008_09
特許番号
US07420056B2

関連ノート

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