1,2-Dichloroethane → HCID 59375005, 화합물

HRID 1811105노트

반응식

HRID 1811105 반응식
[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

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 59375023HCID 59375023, 화합물

생성물 1

HCID 59375005HCID 59375005, 화합물수율 65.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

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, 1 H) 8.24 (br. s., 1 H) 8.20 (s, 1 H) 8.13 (d, J=7.69 Hz, 1 H) 8.05 (d, J=7.91 Hz, 1 H) 7.52-7.68 (m, 3 H) 7.33-7.48 (m, 3 H) 7.13 (d, J=7.69 Hz, 1 H) 7.05 (d, J=8.35 Hz, 1 H) 3.64-3.80 (m, 1 H) 2.69-2.79 (m, 2 H) 1.87-2.00 (m, 2 H) 1.70-1.80 (m, 2 H) 1.48-1.65 (m, 2 H). Mass spectrum m/z 445.2 (M+H)+.

후처리

  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

출처 및 근거

ORD 기록
ord-0016ae49616d4448a3e23bc7e620c50f
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362065B2

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