Diisopropylethylamine → Trifluoroacetic acid

HRID 1162741ノート

反応式

HRID 1162741 の反応式
[F:1][C:2]([F:29])([F:28])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([CH2:12][C:13]([NH:15][C:16]2[S:20][C:19]3[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=3[C:17]=2[C:25]([OH:27])=O)=[O:14])[N:4]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:41]2[N:42]=[CH:43]C=C[C:40]=2[N:39]=N1.C([O:58][C:59](=[O:65])N(CCN)C)(C)(C)C.C(N(CC)C(C)C)(C)C>C(Cl)Cl.CN(C=O)C>[CH3:43][NH:42][CH2:41][CH2:40][NH:39][C:25]([C:17]1[C:18]2[CH2:24][CH2:23][CH2:22][CH2:21][C:19]=2[S:20][C:16]=1[NH:15][C:13](=[O:14])[CH2:12][N:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[C:3]([C:2]([F:28])([F:1])[F:29])=[N:4]1)=[O:27].[C:59]([OH:58])([C:2]([F:29])([F:28])[F:1])=[O:65]

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 2756424N-Boc-N-methylethylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595204832-[2-(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetylamino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid

生成物 2

HCID 6422Trifluoroacetic acid収率 445.9%HCID 529492432-[2-(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetylamino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (2-methylamino-ethyl)-amide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

2-[2-(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetylamino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (25 mg, 0.059 mmol) was dissolved in a solution of DCM (1 mL) and DMF (0.2 mL). O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (27 mg, 0.070 mmol) was added, followed by N-(2-aminoethyl)-N-methyl carbamic acid tert-butyl ester (12 mg, 0.070 mmol) and N,N-diisopropylethylamine (12.2 μL, 0.070 mmol). The resultant mixture was stirred at RT overnight. The solvent was removed under reduced pressure, and the residue obtained purified by preparative reverse phase HPLC. The resulting residue was dissolved in a solution of DCM (0.5 mL) and TFA (0.5 mL) and stirred at RT for 30 min, before concentration in vacuo. The residue obtained was purified by preparative reverse phase HPLC to yield the title compound as a TFA salt (15 mg, 0.025, 42%).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue obtained
  3. custompurified by preparative reverse phase HPLC
  4. dissolutionThe resulting residue was dissolved in a solution of DCM (0.5 mL) and TFA (0.5 mL)
  5. customThe residue obtained
  6. customwas purified by preparative reverse phase HPLC

出典と根拠

ORDレコード
ord-b2e9f6290feb49bf902633aa6f374051
出典データセット
uspto-grants-2010_10
特許番号
US07820707B2

反応ノート

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