1-Hydroxybenzotriazole → 1H-Indole-5-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide

HRID 1178072

反応式

HRID 1178072 の反応式
CCN(C(C)C)C(C)C.[NH:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([NH:21][CH2:22][C:23]([OH:25])=O)=[O:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[N:49]1([C:55]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])=[O:56])[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1>CN(C=O)C.O>[O:25]=[C:23]([N:52]1[CH2:53][CH2:54][N:49]([C:55](=[O:56])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:64])[F:65])[CH2:50][CH2:51]1)[CH2:22][NH:21][C:19]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][CH:11]=[CH:12]2)=[O:20]

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4908648[(1H-Indole-5-carbonyl)-amino]-acetic acidHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochloride

生成物 1

HCID 595596591H-Indole-5-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide収率 45%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (0.111 mL, 0.64 mmol) was added to a stirred solution of [(1H-Indole-5-carbonyl)-amino]-acetic acid (40 mg, 0.18 mmol) in DMF (1.0 mL). HOBT (29 mg, 0.22 mmol) and EDCI.HCl (42 mg, 0.22 mmol) were added, followed by the addition of piperazine-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride (59 mg, 0.20 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. The mixture was then diluted with water and the resulting precipitate was filtered to afford 1H-Indole-5-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide in 45% yield. LC-MS purity: 91%, 1H NMR (CDCl3): δ 8.48 (s, 1H), 8.18 (s, 1H), 7.78-7.54 (m, 4H), 7.42-7.30 (m, 2H), 7.28 (s, 1H), 6.62 (s, 1H), 4.40-4.20 (m, 2H), 4.18-3.82 (m, 2H), 3.78-3.52 (m, 4H), 3.24 (s, 2H).

後処理

  1. filtrationthe resulting precipitate was filtered

出典と根拠

ORDレコード
ord-23a33f6afbf443eab2cec1c9d8274c3b
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

関連ノート

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