Triethylamine → tert-butyl (NZ)-N-[[(2-methylpropan-2-yl)oxycarbonylamino]-[6-(2-phenylethyl)-5-(trifluoromethyl)-1,10-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraen-11-yl]methylidene]carbamate

HRID 1505727Notes

Reaction equation

HRID 1505727 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.[C:26]([NH:33][C:34]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=S)([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C>[C:40]([O:39][C:37](=[O:38])[NH:36]/[C:34](=[N:33]\[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])/[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)([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 5193990N,N'-Di-Boc-thioureaHCID 866919886-Phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole

Product 1

HCID 140613434tert-butyl (NZ)-N-[[(2-methylpropan-2-yl)oxycarbonylamino]-[6-(2-phenylethyl)-5-(trifluoromethyl)-1,10-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraen-11-yl]methylidene]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Mercuric chloride (41 mg, 0.15 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, 53 mg, 0.14 mmol), bis-N-Boc thiourea (38 mg, 0.14 mmol) and triethylamine (0.45 mmol) in DMF (5 mL) at 0° C. After 1 h of stirring at 0° C., ethyl acetate was added. The resulting mixture filtered and the filtrate washed sequentially with water and brine then dried (Na2SO4) and concentrated. The resulting residue was purified by reverse-phase chromatography to yield Z-tert-butyl(((tert-butoxycarbonyl)imino)(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)methyl)carbamate (74 mg, MS m/z=587 (MH+).

Workup

  1. filtrationThe resulting mixture filtered
  2. washthe filtrate washed sequentially with water and brine
  3. dry with materialthen dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe resulting residue was purified by reverse-phase chromatography

Sources & evidence

ORD record
ord-96fee8fac3c649d58ec098b1c013790a
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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