1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57855650、化合物

HRID 1177894ノート

反応式

HRID 1177894 の反応式
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[S:17][C:18]([C:21]([OH:23])=O)=[CH:19][N:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:46][CH2:47][C:48]([N:50]1[CH2:55][CH2:54][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:52][CH2:51]1)=[O:49]>CN(C=O)C.C(OCC)(=O)C.O>[O:49]=[C:48]([N:50]1[CH2:51][CH2:52][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:54][CH2:55]1)[CH2:47][NH:46][C:21]([C:18]1[S:17][C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:20][CH:19]=1)=[O:23]

参加物

9

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1390872-Phenyl-5-carboxythiazoleHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

生成物 1

HCID 57855650HCID 57855650、化合物収率 35.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

DIPEA (170 mg, 0.22 mL, 1.31 mmol) was added to a stirred solution of 2-phenyl-thiazole-5-carboxylic acid (90 mg, 0.43 mmol) in DMF (2 mL). HOBT (71 mg, 0.52 mmol) and EDCI (100 mg, 0.52 mmol) were then added at room temperature. After 2 minutes 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (185 mg, 0.52 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and then extrated with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4 and concentrated under reduced pressure to afford 77.1 mg (35%) of 2-phenyl-thiazole-5-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 95.1%. 1H NMR (DMSO-d6): δ 9.0-8.9 (m, 1H), 8.54-8.5 (s, 1H), 8.0 (m, 2H), 7.9-7.64 (m, 3H), 7.6-7.5 (m, 4H), 4.24-4.1 (m, 2H), 3.8-3.6 (m, 4H), 3.5-3.4 (m, 2H), 3.2-3.0 (m, 2H).

後処理

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c22f8b4734f8402ca27391b94efaccc2
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

反応ノート

読み込み中…