Trifluoroacetic acid → HCID 57418643, 화합물

HRID 2114384노트

반응식

HRID 2114384 반응식
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([CH:7]([NH:14][CH3:15])[CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1.[CH2:22]([O:24][C:25]([C:27]1[CH:28]=[CH:29][C:30]2[O:35][CH2:34][C:33](=[O:36])[N:32]([CH2:37][C:38]([OH:40])=O)[C:31]=2[CH:41]=1)=[O:26])[CH3:23].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.FC(F)(F)C(O)=O>C(Cl)Cl.CC#N.O>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=[CH:5][C:4]([CH:7]([N:14]([CH3:15])[C:38](=[O:40])[CH2:37][N:32]2[C:31]3[CH:41]=[C:27]([C:25]([O:24][CH2:22][CH3:23])=[O:26])[CH:28]=[CH:29][C:30]=3[O:35][CH2:34][C:33]2=[O:36])[CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27567161-([1,1'-Biphenyl]-4-yl)-N-methyl-2-(pyrrolidin-1-yl)ethan-1-amineHCID 57457165HCID 57457165, 화합물

생성물 1

HCID 57418643HCID 57418643, 화합물수율 77.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

[1-(4-biphenylyl)-2-(1-pyrrolidinyl)ethyl]methylamine (0.5 g, 1.8 mmol) and {6-[(ethyloxy)carbonyl]-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl}acetic acid (0.63 g, 2.0 mmol) were dissolved in 10 mL of methylene chloride. Triethylamine (1.0 mL, 7.1 mmol) was delivered to the room temperature mixture, and the solution was allowed to stir for several minutes before a separate solution of 1H-1,2,3-benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP reagent, 0.89 g, 2.0 mmol) dissolved in 4 mL of methylene chloride was added at room temperature to the mixture. The reaction was maintained at that temperature for 72 hours, before it was determined to be complete by LCMS (two Aquasil C18, 20×1 mm columns were run in sequence, 4 minutes at 0.1 mL/min, 1-99% CH3CN/H2O with 0.018% trifluoroacetic acid, ES) Rt=2.7 min and m/e 542 [M+1]+. Solvent was removed by rotary evaporation and the crude residue was purified by prep HPLC (Waters, 50×100 mm, 84 mL/min, A: acetonitrile B: water (pH=10, NH4OH), A: 10 to 99% over 15 min, UV detection at 214 nm) to give the title compound (0.75 g. 1.4 mmol, 77%) as a pale yellow amorphous solid. MS (ES) m/e 542 [M+H]+.

후처리

  1. customwas delivered to the room temperature mixture
  2. additionwas added at room temperature to the mixture
  3. temperatureThe reaction was maintained at that temperature for 72 hours, before it
  4. customSolvent was removed by rotary evaporation
  5. customthe crude residue was purified by prep HPLC (Waters, 50×100 mm, 84 mL/min

출처 및 근거

ORD 기록
ord-e5535e73a2104af7a5e01095fa71e72c
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432258B2

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