Triethylamine → tert-butyl (2-oxo-2-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethyl)carbamate

HRID 1505729Notes

Reaction equation

HRID 1505729 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH2:32]([C:40]1[C:41]([C:53]([F:56])([F:55])[F:54])=[C:42]2[C:46]3=[C:47]([CH2:49][NH:50][CH2:51][CH2:52][N:45]3[CH:44]=[CH:43]2)[CH:48]=1)[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl.[C:58]([NH:65][CH2:66][C:67](O)=[O:68])([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59]>C1COCC1>[O:68]=[C:67]([CH:51]1[NH:50][CH2:49][C:47]2=[C:46]3[C:42](=[C:41]([C:53]([F:56])([F:55])[F:54])[C:40]([CH2:32][CH2:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:48]2)[CH:43]=[CH:44][N:45]3[CH2:52]1)[CH2:66][NH:65][C:58](=[O:59])[O:60][C:61]([CH3:63])([CH3:62])[CH3:64]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 19004789N-Boc-glycine hydrochlorideHCID 866919886-Phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole

Product 1

HCID 86692000tert-butyl (2-oxo-2-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

HATU (172 mg, 0.45 mmol) and triethylamine (1.97 mmol) was added to 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, 150 mg, 0.39 mmol) and N-Boc-glycine hydrochloride (72 mg, 0.41 mmol) in THF (7 mL). After stirring overnight, the resulting mixture was partitioned between ethyl acetate and water. The organic phase was washed sequentially with NaHCO3 (sat'd., aq) and brine, then dried and concentrated. The resulting residue was purified by reverse-phase chromatography to yield tert-butyl (2-oxo-2-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethyl)carbamate (200 mg, MS m/z 502 (MH+).

Workup

  1. customthe resulting mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed sequentially with NaHCO3 (sat'd., aq) and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting residue was purified by reverse-phase chromatography

Sources & evidence

ORD record
ord-ed4aaa68e64445aa8bf118ba40d17a5a
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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