Tetrahydrofuran → HCID 178438686, 화합물

HRID 2062525노트

반응식

HRID 2062525 반응식
[O:1]=[C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)=[C:6]([CH2:23][CH2:24][CH3:25])[N:5]2[N:26]=[CH:27][N:28]=[C:4]2[N:3]1[CH:29]1[CH2:41][CH2:40][C:32]2([O:36][C@H:35]3[CH2:37][O:38][CH2:39][C@H:34]3[O:33]2)[CH2:31][CH2:30]1.C([BH3-])#N.[Na+].O1CCCC1>C(OCC)(=O)C>[OH:36][C@H:35]1[CH2:37][O:38][CH2:39][C@H:34]1[O:33][C@H:32]1[CH2:31][CH2:30][C@H:29]([N:3]2[C:2](=[O:1])[C:7]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]4[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:11][CH:10]=3)=[C:6]([CH2:23][CH2:24][CH3:25])[N:5]3[N:26]=[CH:27][N:28]=[C:4]23)[CH2:41][CH2:40]1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 670095474'-({5-oxo-7-propyl-4-[(3a'R,6a'S)-tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxol]-4-yl]-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile

생성물 1

HCID 178438686HCID 178438686, 화합물수율 18.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

A mixture of 4′-({5-oxo-7-propyl-4-[(3a′R,6a′S)-tetrahydrospiro[cyclohexane-1,2′-furo[3,4-d][1,3]dioxol]-4-yl]-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile (0.77 g), sodium cyanoborohydride (0.45 g), boron trifluoride-diethyl ether complex (0.88 mL) and tetrahydrofuran (20 mL) was stirred at 70° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.14 g, 18%).

후처리

  1. washwashed with water
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d87687c256cf40158cb91137097655c0
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283353B2

반응 노트

불러오는 중…