Triethylamine → 4-bromo-N-[(cis)-2-hydroxycyclohexyl]quinoline-2-carboxamide

HRID 1497321노트

반응식

HRID 1497321 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.[Cl-].[OH:16][C@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[NH3+:23].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:23][C@@H:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C@@H:17]2[OH:16])=[O:14])[CH:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11263589[(1R,2S)-2-hydroxycyclohexyl]azanium;chlorideHCID 155308124-Bromoquinoline-2-carboxylic acid

생성물 1

HCID 673239414-bromo-N-[(cis)-2-hydroxycyclohexyl]quinoline-2-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of the 4-bromoquinoline-2-carboxylic acid (A3) (0.10 g, 0.40 mmol) in 2.0 mL, CH2Cl2 was added (cis)-2-hydroxycyclohexanaminium chloride (0.12 g, 0.80 mmol), BOP reagent (0.35 g, 0.80 mmol), and triethylamine (0.16 mL, 1.2 mmol). The reaction mixture was stirred at room temperature for 16 h, diluted with CH2Cl2, washed with water, dried over sodium sulfate, filtered, and concentrated. The resultant residue subjected to silica gel chromatography eluting with 0-60% ethyl acetate in hexanes to afford 4-bromo-N-[(cis)-2-hydroxycyclohexyl]quinoline-2-carboxamide (I1) that gave a mass ion (ES+) of 349.2 (79Br) for M+H+.

후처리

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluting with 0-60% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-04f8c1f59127471e920f94450027aa78
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199939B2

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