(3S)-pyrrolidin-3-ol → (S)-4-[4-(3-hydroxy-pyrrolidin-1-yl)-2-methyl-quinolin-7-yloxymethyl]-benzonitrile

HRID 2415502노트

반응식

HRID 2415502 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:22])[CH:3]=1.[OH:23][C@H:24]1[CH2:28][CH2:27][NH:26][CH2:25]1>>[OH:23][C@H:24]1[CH2:28][CH2:27][N:26]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:12][CH2:13][C:14]4[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=4)=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:22])[CH:3]=2)[CH2:25]1

참가 물질

3

반응물 2

HCID 2733874(3S)-pyrrolidin-3-olHCID 22641336HCID 22641336, 화합물

생성물 1

HCID 10109108(S)-4-[4-(3-hydroxy-pyrrolidin-1-yl)-2-methyl-quinolin-7-yloxymethyl]-benzonitrile수율 87.7%

실험 절차

A solution of 1.42 g of (4.6 mmol) of 4-(4-chloro-2-methyl-quinolin-7-yloxymethyl)-benzonitrile and 1.11 g (12.5 mmol) of (S)-3-hydroxypyrrolidine in 1-methyl-2-pyrrolidine (25 ml) was heated under nitrogen at 100° C. (oil bath temperature) for 23 h. The reaction mixture was concentrated in a high vacuum, the residue taken up in methylene chloride, which was washed with water, saturated NaCl solution and then dried over magnesium sulphate. The solvent was removed in vacuo, the residue triturated with MeOH, filtered off by suction, washed subsequently with MeOH and ether and then dried in a high vaccum to give 1.45 g (83.86%) of the (S)-4-[4-(3-hydroxy-pyrrolidin-1-yl)-2-methyl-quinolin-7-yloxymethyl]-benzonitrile as a brown solid. ISP mass spectrum, m/e: 360.2 (M+1 calculated for C22H21N3O2: 360.2).

후처리

  1. concentrationThe reaction mixture was concentrated in a high vacuum
  2. washwhich was washed with water, saturated NaCl solution
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was removed in vacuo
  5. customthe residue triturated with MeOH
  6. filtrationfiltered off by suction
  7. washwashed subsequently with MeOH and ether
  8. customdried in a high vaccum

출처 및 근거

ORD 기록
ord-491498adb21a4df6ad5b9f86b9b0001b
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06818767B2

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