Triethylamine → 3,3,3-trifluoro-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)propan-1-one

HRID 1505731Notes

Reaction equation

HRID 1505731 reaction equation
[CH2:1]([C:9]1[C:10]([C:22]([F:25])([F:24])[F:23])=[C:11]2[C:15]3=[C:16]([CH2:18][NH:19][CH2:20][CH2:21][N:14]3[CH:13]=[CH:12]2)[CH:17]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:26][C:27]([F:34])([F:33])[CH2:28][CH2:29]C(O)=O.CN(C([O:42]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C1COCC1>[F:26][C:27]([F:34])([F:33])[CH2:28][C:29]([CH:20]1[NH:19][CH2:18][C:16]2=[C:15]3[C:11](=[C:10]([C:22]([F:25])([F:24])[F:23])[C:9]([CH2:1][CH2:2][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:17]2)[CH:12]=[CH:13][N:14]3[CH2:21]1)=[O:42]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27770854,4,4-Trifluorobutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866919886-Phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole

Product 1

HCID 866920023,3,3-trifluoro-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)propan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (prepared as described in Example 2 above, 66 mg, 0.17 mmol), 3-trifluoromethylpropionic acid (23 mg, 0.18 mmol), HATU (75 mg, 0.2 mmol) and triethylamine (87 mg, 0.86 mmol) in THF (7 mL) was stirred overnight. The resulting mixture was partitioned between etyl acetate and water, and the organic layer was washed sequentially with NaHCO3 (sat'd) and brine, then dried (Na2SO4) and concentrated. The residue was purified by reverse-phase chromatography (CH3CN/H2O-TFA) to yield 3,3,3-trifluoro-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)propan-1-one.

Workup

  1. customThe resulting mixture was partitioned between etyl acetate and water
  2. washthe organic layer was washed sequentially with NaHCO3 (sat'd) and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by reverse-phase chromatography (CH3CN/H2O-TFA)

Sources & evidence

ORD record
ord-5ce1aff59e324a00a573d6648955ace1
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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