Acetonitrile → (2S,4S)-4-Fluoro-1-[({1-[4-(trifluoromethyl)phenyl]piperidin-4-yl}amino)acetyl]pyrrolidine-2-carbonitrile hydrochloride

HRID 350857

반응식

HRID 350857 반응식
[ClH:1].[F:2][C:3]([F:18])([F:17])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.Br[CH2:20][C:21]([N:23]1[CH2:27][C@@H:26]([F:28])[CH2:25][C@H:24]1[C:29]#[N:30])=[O:22].C(N(CC)CC)C.C(#N)C>Cl.O1CCOCC1.CC(C)=O.CCOCC>[ClH:1].[F:28][C@@H:26]1[CH2:27][N:23]([C:21](=[O:22])[CH2:20][NH:16][CH:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([F:2])([F:17])[F:18])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)[C@H:24]([C:29]#[N:30])[CH2:25]1

참가 물질

8

반응물 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 210903881-(4-(Trifluoromethyl)phenyl)piperidin-4-amine hydrochlorideHCID 21090395(2S,4S)-1-(2-bromoacetyl)-4-fluoropyrrolidine-2-carbonitrile

생성물 1

HCID 69515823(2S,4S)-4-Fluoro-1-[({1-[4-(trifluoromethyl)phenyl]piperidin-4-yl}amino)acetyl]pyrrolidine-2-carbonitrile hydrochloride수율 47.5%

시약·촉매·용매 3

HCID 313Hydrochloric Acid촉매HCID 312751,4-Dioxane용매HCID 21584533Acetone diethylether용매

실험 절차

A round bottom flask was mixed with 1-[4-(trifluoromethyl)phenyl]piperidin-4-amine hydrochloride (337 mg, 1.34 mmol), (2S,4S)-1-(bromoacetyl)-4-fluoropyrrolidine-2-carbonitrile (316 mg, 1.34 mmol), trietylamine (408 mg, 04.03 mmol) and acetonitrile (20 mL). The reaction mixture was allowed to stir at RT for 17.0 hours. The reaction mixture was concentrated to dryness. The reaction mixture was partitioned between EtOAc and saturated NaHCO3 and the organics were dried over MgSO4. The organics were concentrated to dryness and dried in vacuo. The resulting crude solid was purified using silica gel chromatography (99% CH2Cl2/1% MeOH, with 1.7% NH3) to yield a pure solid. The solid was dissolved into a 1/1 acetone/ether solution and mixed with several drops of 4.0 N HCl in 1,4-dioxane. The resulting solid was filtered and dried in vacuo to give a total of 277 mg of pure solid.

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customThe reaction mixture was partitioned between EtOAc and saturated NaHCO3
  3. dry with materialthe organics were dried over MgSO4
  4. concentrationThe organics were concentrated to dryness
  5. customdried in vacuo
  6. customThe resulting crude solid was purified
  7. customto yield a pure solid
  8. filtrationThe resulting solid was filtered
  9. customdried in vacuo

출처 및 근거

ORD 기록
ord-7c0757c11a3c4bd28b83561237d1abcd
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183290B2

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