Acetic Acid → HCID 178474975, 화합물

HRID 2042429노트

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HRID 2042429 반응식
Cl.Cl.Cl.[O:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[CH2:6][CH2:5]1.C(N(CC)C(C)C)(C)C.[C:37](O)(=[O:39])[CH3:38].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[OH-].[Na+]>CN(C=O)C>[O:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH:27][C:37](=[O:39])[CH3:38])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[CH2:6][CH2:5]1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178478589HCID 178478589, 화합물2회

생성물 1

HCID 178474975HCID 178474975, 화합물수율 99%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of trans-4-{2-[4-(2,3-dihydrofuro[3,2-c]pyridin-4-yl)-piperazin-1-yl]-ethyl}-cyclohexanamine trihydrochloride (intermediate C) (110 mg, 0.25 mmol) in DMF (1.8 ml) was added N,N-diisopropylethylamine (210 mg, 278 μl, 1.63 mmol), acetic acid (18.0 mg, 17.2 μl, 300 μmol) and TBTU (128 mg, 400 μmol). The mixture was allowed to stir at room temperature for 4 h. The mixture was added to ice/water (5 ml) and 1N NaOH (5 ml) and extracted with dichloromethane/MeOH (9:1, 20 ml). The organic phase was washed with brine (20 ml), dried (MgSO4) and evaporated. The crude material (0.15 g) was triturated with dichloromethane (2 ml) and diethyl ether (5 ml) for ½ h, the precipitate was collected by filtration, washed with diethyl ether and dried to yield the title compound as off-white solid (92 mg, 99%), MS (ISP) m/z=373.2 [(M+H)+], mp 260° C.

후처리

  1. extractionextracted with dichloromethane/MeOH (9:1, 20 ml)
  2. washThe organic phase was washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude material (0.15 g) was triturated with dichloromethane (2 ml) and diethyl ether (5 ml) for ½ h
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with diethyl ether
  8. customdried

출처 및 근거

ORD 기록
ord-9ce63bc6f5f541e5bcc8ec7e1dafc2f8
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586579B2

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