Trifluoroacetic acid → HCID 67125813、化合物

HRID 2042409ノート

反応式

HRID 2042409 の反応式
[CH3:1][C:2]1[C:3]2[O:23][CH:22]=[CH:21][C:4]=2[C:5]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[C:3]2[O:23][CH:22]=[CH:21][C:4]=2[C:5]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67125779HCID 67125779、化合物

生成物 1

HCID 67125813HCID 67125813、化合物収率 79.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A stirred solution of tert-butyl 4-(7-methyl-furo[3,2-c]pyridin-4-yl)-piperazine-1-carboxylate (step A) (2.34 g, 7.37 mmol) in dichloromethane (4.1 ml) was cooled to 0° C., trifluoroacetic acid (8.41 g, 5.68 ml, 73.7 mmol) was added drop wise and the reaction mixture was allowed to stir for 10 min at 0° C. and for 30 min at room temperature. The solution was poured onto ice and 2N sodium carbonate solution (50 ml) and extracted with dichloromethane (2×25 ml). The combined organic layers were washed with brine (30 mL), dried (MgSO4) and evaporated. The crude product (1.59 g) was further purified by flash chromatography on silica gel (100% dichloromethane/MeOH/NH4OH 80:10:1) to yield 7-methyl-4-(piperazin-1-yl)-furo[3,2-c]pyridine as a yellow solid (1.27 g, 79%), MS (ISP) m/z=218.4 [(M+H)+], mp 111.5° C.

後処理

  1. extractionextracted with dichloromethane (2×25 ml)
  2. washThe combined organic layers were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product (1.59 g) was further purified by flash chromatography on silica gel (100% dichloromethane/MeOH/NH4OH 80:10:1)

出典と根拠

ORDレコード
ord-05393eb23f4a4c91a84196bcd4a80fc5
出典データセット
uspto-grants-2013_11
特許番号
US08586579B2

反応ノート

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