Trifluoroacetic acid → HCID 57488843、化合物

HRID 2114408ノート

反応式

HRID 2114408 の反応式
[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.[O:22]=[C:23]1[N:27]([CH2:28][C:29]([OH:31])=O)[C:26]2[CH:32]=[C:33]([O:36][C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:35][C:25]=2[O:24]1.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>CN(C)C=O.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:29](=[O:31])[CH2:28][N:27]2[C:26]3[CH:32]=[C:33]([O:36][C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:35][C:25]=3[O:24][C:23]2=[O:22])[CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2756716(1-Biphenyl-4-yl-2-pyrrolidin-1-yl-ethyl)-methyl-amineHCID 57488865HCID 57488865、化合物

生成物 1

HCID 57488843HCID 57488843、化合物収率 6.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

[1-(4-biphenylyl)-2-(1-pyrrolidinyl)ethyl]methylamine (0.09 g, 0.32 mmol) and [2-oxo-5-[(trifluoromethyl)oxy]-1,3-benzoxazol-3(2H)-yl]acetic acid (0.097 g, 0.35 mmol) were dissolved in 1 mL of dimethylformamide. Triethylamine (0.13 mL, 0.96 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, 0.155 g, 0.32 mmol) dissolved in 1 mL of dimethylformamide was added to the mixture at room temperature. The reaction was maintained at that temperature for 18 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=2.0 min and m/e 541 [M+1]+. The reaction mixture was filtered through a 0.45 μm PTFE Acrodisk and the crude residue was purified by prep HPLC (Waters, 30×75 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 (0.011 g. 0.02 mmol, 6%) as an off-white amorphous solid. MS (ES) m/e 541 [M+H]+.

後処理

  1. customwas delivered to the room temperature mixture
  2. additionwas added to the mixture at room temperature
  3. temperatureThe reaction was maintained at that temperature for 18 hours, before it
  4. filtrationThe reaction mixture was filtered through a 0.45 μm PTFE Acrodisk
  5. customthe crude residue was purified by prep HPLC (Waters, 30×75 mm, 84 mL/min

出典と根拠

ORDレコード
ord-7e67934b06f34b91a4114856ca6acbd6
出典データセット
uspto-grants-2008_10
特許番号
US07432258B2

反応ノート

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