1,2-Dichloroethane → HCID 59375005、化合物

HRID 661924ノート

反応式

HRID 661924 の反応式
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17](O)=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:50][N:51]1[CH2:56][CH2:55][CH:54]([NH2:57])[CH2:53][CH2:52]1>C1COCC1.CN(C=O)C>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:7]1[C:8]2[C:9]3[C:14](=[CH:13][C:12]([C:17]([NH:57][CH:54]4[CH2:55][CH2:56][N:51]([CH3:50])[CH2:52][CH2:53]4)=[O:18])=[CH:11][CH:10]=3)[NH:15][C:16]=2[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 59375023HCID 59375023、化合物

生成物 1

HCID 59375005HCID 59375005、化合物収率 65.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazole-2-carboxylic acid (Example 23-2, 30 mg, 0.086 mmol), EDC (23.11 mg, 0.121 mmol), HOBT (18.46 mg, 0.121 mmol), DIEA (30 μL, 0.172 mmol), and 1-methylpiperidin-4-amine (9.83 mg, 0.086 mmol) in THF and DMF (4:1, 2 mL) was stirred at rt overnight. The mixture was concentrated and purified by preparative HPLC. The isolated product was partitioned between DCM and NaHCO3 (aq). The organic phase was dried and concentrated to provide 4-(2-fluorophenyl)-N7-(1-methylpiperidin-4-yl)-9H-carbazole-1,7-dicarboxamide as a white solid (25 mg, 62%). 1H NMR (400 MHz, DMSO-d6) δ 11.75 (s, 1H) 8.24 (br. s., 1H) 8.20 (s, 1H) 8.13 (d, J=7.69 Hz, 1H) 8.05 (d, J=7.91 Hz, 1H) 7.52-7.68 (m, 3H) 7.33-7.48 (m, 3H) 7.13 (d, J=7.69 Hz, 1H) 7.05 (d, J=8.35 Hz, 1H) 3.64-3.80 (m, 1H) 2.69-2.79 (m, 2H) 1.87-2.00 (m, 2H) 1.70-1.80 (m, 2H) 1.48-1.65 (m, 2H). Mass spectrum m/z 445.2 (M+H)+.

後処理

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC
  3. customThe isolated product was partitioned between DCM and NaHCO3 (aq)
  4. customThe organic phase was dried
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-7c00a63ef34d45ff98571a681ba2da3b
出典データセット
uspto-grants-2011_12
特許番号
US08084620B2

反応ノート

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