Dimethylformamide → HCID 23150566、化合物

HRID 228035

反応式

HRID 228035 の反応式
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

参加物

7

反応物 5

HCID 6228Dimethylformamide2 回HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23150613HCID 23150613、化合物HCID 231506694,4-Difluorocyclohexan-1-amine hydrochloride

生成物 1

HCID 23150566HCID 23150566、化合物

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-31c91e7700664c3c8f91c6486ccfa022
出典データセット
uspto-grants-2009_07
特許番号
US07560569B2

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