Triethylamine → 1-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

HRID 1748352Notes

Reaction equation

HRID 1748352 reaction equation
[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([OH:18])=O)=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[C:52]([N:71]1[CH:75]=[C:74]([C:76]2[CH:77]=[C:78]([CH:80]=[CH:81][CH:82]=2)[NH2:79])[N:73]=[CH:72]1)([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.C(N(CC)CC)C>CN(C=O)C.O>[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([NH:79][C:78]4[CH:80]=[CH:81][CH:82]=[C:76]([C:74]5[N:73]=[CH:72][N:71]([C:52]([C:65]6[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=6)([C:59]6[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=6)[C:53]6[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=6)[CH:75]=5)[CH:77]=4)=[O:18])=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 114751133-(1-trityl-1H-imidazol-4-yl)anilineHCID 672357061-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid2×

Product 1

HCID 683235541-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 61 mg, 0.25 mmol) in DMF (1.5 mL) is added benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (194 mg, 0.37 mmol). The reaction mixture is stirred for 10 min and 3-(1-trityl-1H-imidazol-4-yl)aniline (100 mg, 0.25 mmol) and triethylamine (0.07 mL, 0.50 mmol) are added. The reaction mixture is stirred at room temperature for 16 h. Water (35 mL) is added and the resulting solid is collected by filtration and rinsed with water to afford the title crude compound which is used in the next step without purification.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 16 h
  2. filtrationthe resulting solid is collected by filtration
  3. washrinsed with water

Sources & evidence

ORD record
ord-487920a234e647e28ddda1ea997046bd
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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