Dimethylformamide → HCID 23150566, 화합물

HRID 228035

반응식

HRID 228035 반응식
O[N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2N=N1.[CH2:11]([O:18][C:19](C12CCC(C(O)=O)(CC1)CC2)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.CN(C)CCCN=C=N[CH2:41][CH3:42].Cl.[F:45][C:46]1([F:53])[CH2:51][CH2:50][CH:49]([NH2:52])[CH2:48][CH2:47]1.CN(C)[CH:56]=[O:57]>C(N(CC)CC)C>[CH2:11]([O:18][C:19]([NH:2][C:6]12[CH2:42][CH2:41][C:9]([C:56]([NH:52][CH:49]3[CH2:50][CH2:51][C:46]([F:53])([F:45])[CH2:47][CH2:48]3)=[O:57])([CH2:8][CH2:7]1)[CH2:10][CH2:5]2)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 5

HCID 6228Dimethylformamide2회HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 231506134-Benzyloxycarbonylbicyclo[2.2.2]octane-1-carboxylic acidHCID 231506694,4-Difluorocyclohexan-1-amine hydrochloride

생성물 1

HCID 23150566HCID 23150566, 화합물

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

1-Hydroxybenzotriazole (138 mg), 4-benzyloxycarbonylbicyclo[2.2.2]octane-1-carboxylic acid (72.0 mg) and N,N-dimethylformamide (8 mL) were mixed together. While the mixture was chilled in an ice bath, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (265 mg) was added and the mixture was stirred at room temperature for 1 hour. Subsequently, a mixture of 4,4-difluorocyclohexylamine hydrochloride (108 mg), triethylamine (105 μL) and N,N-dimethylformamide (2 mL) was added and the resultant mixture was stirred at room temperature for 18 hours and was then concentrated under reduced pressure. Water (10 mL) was added to the residue and the solution was extracted with ethyl acetate (3×10 mL). The ethyl acetate extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by a silica gel column (eluant:hexane:ethyl acetate=3:1) to give 4-benzyloxycarbonylamino-N-(4,4-difluorocyclohexyl)bicyclo[2.2.2]octane-1-carboxamide (57.0 mg) as a white solid.

후처리

  1. temperatureWhile the mixture was chilled in an ice bath
  2. additionwas added
  3. concentrationwas then concentrated under reduced pressure
  4. additionWater (10 mL) was added to the residue
  5. extractionthe solution was extracted with ethyl acetate (3×10 mL)
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by a silica gel column (eluant:hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-31c91e7700664c3c8f91c6486ccfa022
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560569B2

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