Diisopropylethylamine → HCID 58062981, 화합물

HRID 659230

반응식

HRID 659230 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([O:16][CH3:17])[C:4]=1[C:5](O)=[O:6].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.Cl.[N:55]1([C@H:60]2[CH2:65][CH2:64][CH2:63][CH2:62][C@H:61]2[NH2:66])[CH2:59][CH2:58][CH2:57][CH2:56]1>CN(C)C=O>[CH3:17][O:16][C:8]1[CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=[C:3]([C:2]([F:1])([F:18])[F:19])[C:4]=1[C:5]([NH:66][C@@H:61]1[CH2:62][CH2:63][CH2:64][CH2:65][C@@H:60]1[N:55]1[CH2:56][CH2:57][CH2:58][CH2:59]1)=[O:6]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27412872-Methoxy-4,6-bis(trifluoromethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66680564cis-2-Pyrrolidin-1-yl-cyclohexylamine dihydrochloride2회

생성물 1

HCID 58062981HCID 58062981, 화합물수율 52.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2,4-Bis(trifluoromethyl)-6-methoxy-benzoic acid (200 mg, 0.69 mmol) was dissolved in 5 mL dimethylformamide. N,N-Diisopropyl ethyl amine (359 mg, 2.8 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (264 mg, 0.69 mmol) were added. After 5 minutes of stirring at room temperature cis-2-pyrrolidin-1-yl-cyclohexylamine dihydrochloride (intermediate F) (171 mg, 0.71 mmol) was added. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated off. The residue was taken up in 2N sodium carbonate solution and ethyl acetate and was extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0→140:10:1) yielded cis-2-methoxy-N-(2-pyrrolidin-1-yl-cyclohexyl)-4,6-bis-trifluoromethyl-benzamide as a white solid (158 mg, 52%), MS: m/e=439.2 [(M+H)+].

후처리

  1. additionwas added
  2. customThe solvent was evaporated off
  3. extractionethyl acetate and was extracted three times with ethyl acetate
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0→140:10:1)

출처 및 근거

ORD 기록
ord-eb70b7417188446885fccc12434d259f
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080541B2

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