Triethylamine → 7-chloro-2-[(S)-2-([t-butyldimethylsilyloxy]methyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine

HRID 985191노트

반응식

HRID 985191 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][CH2:15][C@H:14]3[CH2:18][OH:19])=[O:12])[S:10][C:3]=12.[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21].C(N(CC)CC)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][CH2:15][C@H:14]3[CH2:18][O:19][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26])=[O:12])[S:10][C:3]=12

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 207677577-chloro-2-[(S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine

생성물 1

HCID 207677677-chloro-2-[(S)-2-([t-butyldimethylsilyloxy]methyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine수율 126.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a stirred solution of 7-chloro-2-[(S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 3a (4.50 g, 15 mmole) were added t-butyldimethylchlorosilane (3.18 g, 21 mmole) and triethylamine (3.4 ml, 2.47 g, 24 mmole). The resultant reaction mixture was stirred at ambient temperaure for 16 hours. The crude reaction mixture was poured into water (150 ml) and extracted with CH2Cl2 (150 ml). The combined organic extracts were washed with brine (150 ml), dried over Na2SO4 and concentrated, in vacuo, to give 7.8 g of an orange syrup, which was purified by silica gel chromatography. Elution with Et2O:hexane (67:33) and evaporation of the appropriate fractions gave 5.73 g (92%) of an off-white solid. 1H NMR (DMSO-d6): δ8.72 (1H, d, J=5.0 Hz), 8.07 (1H, s), 7.68 (1 H, d, J=5.0 Hz), 4.30-4.15 (1H, m), 3.94-3.67 (4H, m), 2.12-1.81 (4H, m), 0.85 (9H, s), 0.03 (3H, s), 0.00 (3H, s). Anal. Calcd. for C19H27N2O2SClSi: C, 55.52; H, 6.62; N, 6.82; S, 7.80; Cl, 8.63. Found: C, 55.49; H, 6.46; N, 6.92; S, 7.80; Cl, 8.88.

후처리

  1. customThe resultant reaction mixture
  2. customThe crude reaction mixture
  3. extractionextracted with CH2Cl2 (150 ml)
  4. washThe combined organic extracts were washed with brine (150 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated, in vacuo

출처 및 근거

ORD 기록
ord-429e5074fe824167b4df19ac39e7872c
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06869962B2

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