Ammonia → 9-[(Cyclopentyl)methyl]-4-hydroxy-5-carbamoyl carbazole

HRID 51458노트

반응식

HRID 51458 반응식
[CH:1]1([CH2:6][N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:20])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][C:12]=3[C:21]([O:23]C)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:25]>C1COCC1.[OH-].[NH4+]>[CH:1]1([CH2:6][N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:20])[C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][C:12]=3[C:21](=[O:23])[NH2:25])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 227382539-[(Cyclopentyl)methyl]-4-hydroxy-5-carbomethoxy carbazole

생성물 1

HCID 227382079-[(Cyclopentyl)methyl]-4-hydroxy-5-carbamoyl carbazole

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 14923Ammonium Hydroxide용매

반응 조건

온도
35 °C

실험 절차

A solution of 9-[(cyclopentyl)methyl]-4-hydroxy-5-carbomethoxy carbazole (110 mg, 0.34 mmol) in 3 mL of THF and 20 mL of concentrated aqueous ammonium hydroxide was treated with a stream of NH3 gas to ensure saturation. The reaction vessel was capped, and the mixture heated to 35° C. with stirring until tlc indicated complete consumption of starting material (20 h). The THF was evaporated, and the aqueous layer was filtered. The resultant solid was triturated with ether to afford 50 mg (0.162; 48%) of the title compound as a greenish-white solid. IR (KBr, cm−1) 3416, 3199, 3126, 1630, 1599. 1442, 1262, 778. 'FAB HRMS m/e, Calcd for C20H21N2O2: 309.1603. Found: 309.1607 (M+1).

후처리

  1. customThe reaction vessel was capped
  2. customconsumption of starting material (20 h)
  3. customThe THF was evaporated
  4. filtrationthe aqueous layer was filtered
  5. customThe resultant solid was triturated with ether

출처 및 근거

ORD 기록
ord-0ed2252eb6d5453087a00cbd681d3793
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713645B1

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