Triethylamine → (2-(3-(2-Hydroxyethyl)benzyl)-5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)(5-methylthiophen-2-yl)methanone

HRID 471043노트

반응식

HRID 471043 반응식
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1.Cl.[CH3:13][C:14]1[S:18][C:17]([C:19]([N:21]2[CH2:29][C:25]3([CH2:28][NH:27][CH2:26]3)[O:24][CH2:23][CH2:22]2)=[O:20])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(#N)C>[OH:11][CH2:10][CH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:27]1[CH2:26][C:25]2([CH2:29][N:21]([C:19]([C:17]3[S:18][C:14]([CH3:13])=[CH:15][CH:16]=3)=[O:20])[CH2:22][CH2:23][O:24]2)[CH2:28]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 67292541(5-Methylthiophen-2-yl)(5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)methanone hydrochloride

생성물 1

HCID 57989289(2-(3-(2-Hydroxyethyl)benzyl)-5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)(5-methylthiophen-2-yl)methanone

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

2-(3-(Bromomethyl)phenyl)ethanol (example 6, step a) (0.281 g) was added to a solution of (5-methylthiophen-2-yl)(5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)methanone hydrochloride (example 33, step h) (0.29 g) and triethylamine (0.42 mL) in acetonitrile (15 mL) at 20° C. and the resultant mixture stirred for 3 hours at 20° C. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic layer was dried over sodium sulphate, filtered and the solvent removed under reduced pressure. The crude product was purified by flash silica chromatography using 3% methanol in dichloromethane with 1% triethylamine as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.32 g.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and brine
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-c696b522d52d402c8588da8404308251
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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