Trifluoroacetic acid → Bavisant

HRID 604257ノート

反応式

HRID 604257 の反応式
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:22](OC(N1CCN(C(=O)C2C=CC(CN3CCOCC3)=CC=2)CC1)=O)([CH3:25])(C)[CH3:23].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:25]1([N:19]2[CH2:18][CH2:17][N:16]([C:14]([C:11]3[CH:10]=[CH:9][C:8]([CH2:7][N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[CH:13][CH:12]=3)=[O:15])[CH2:21][CH2:20]2)[CH2:22][CH2:23]1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acid2 回HCID 592181854-(4-Morpholin-4-ylmethyl-benzoyl)piperazine-1-carboxylic acid tert-butyl esterHCID 59218186(4-Morpholin-4-ylmethyl-phenyl)piperazin-1-yl-methanone

生成物 1

HCID 16061509Bavisant収率 30%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(4-Morpholin-4-ylmethyl-phenyl)-piperazin-1-yl-methanone. A solution of 4-(4-morpholin-4-ylmethyl-benzoyl)-piperazine-1-carboxylic acid tert -butyl ester (1.163 g) in CH2Cl2 (10 mL) was treated with TFA (˜4 mL). After 30 min, additional TFA (5 mL) was added, and the mixture was stirred for a further 2 h. The mixture was diluted with diluted with satd. aq. NaHCO3 and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (SiO2) to give the title compound (0.255 g, 30%). MS (ESI): mass calcd. for C16H23N3O2, 289.18; m/z found, 290.4 [M+H]+. 1H NMR (CDCl3): 7.41-7.35 (m, 4H), 3.95-3.70 (m, 6H), 3.52 (s, 2H), 3.09-2.80 (m, 6H), 2.49-2.42 (m, 4H).

後処理

  1. additionThe mixture was diluted
  2. additionwith diluted with satd
  3. extractionaq. NaHCO3 and extracted with CH2Cl2
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (SiO2)

出典と根拠

ORDレコード
ord-c01190cbecf44e2f952b206f842e7bf7
出典データセット
uspto-grants-2011_03
特許番号
US07910582B2

反応ノート

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