Diisopropylethylamine → Trifluoroacetic acid

HRID 1162741Notes

Reaction equation

HRID 1162741 reaction equation
[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]

Participants

8

Reactant 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

Product 2

HCID 6422Trifluoroacetic acidYield 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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b2e9f6290feb49bf902633aa6f374051
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

Loading…