Triethylamine → 4-[(6-Oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-ylcarbamoyl)-methyl]-piperazine-1-carboxylic acid tert-butyl ester
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:6]3=[C:7]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[NH:8][C:9]([CH:10]=1)=[C:5]23.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36](O)=[O:37])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(Cl)Cl.CO.CN(C)C=O>[C:22]([O:26][C:27]([N:29]1[CH2:30][CH2:31][N:32]([CH2:35][C:36](=[O:37])[NH:1][C:2]2[CH:3]=[C:4]3[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:6]4=[C:7]([C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=5)[NH:8][C:9]([CH:10]=2)=[C:5]34)[CH2:33][CH2:34]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]Participants
7
Reactant 4
HCID 8471Triethylamine
HCID 27356422-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}acetic acid
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 1357740798-Amino-2-phenyl-1,5-dihydro-[1,2]diazepino[4,5,6-cd]indol-6-oneProduct 1
Reagents, catalysts & solvents 2
Procedure
Preparation of example 27 from the title compound of Example 7 (0.025 g, 0.09 mmol), 4-carboxymethyl-piperazine-1-carboxylic acid tert-butyl ester (0.044 g, 0.18 mmol), triethylamine (0.05 mL, 0.4 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (38 mg, 0.1 mmol) and N,N-dimethylformamide (0.05 M, 1.8 mL) was carried out analogously to Example 11. Silica gel chromatography (95:5 CH2Cl2/methanol), also in an analogous manner, afforded the title compound (15 mg) as a yellow powder in 33% yield.
Sources & evidence
- ORD record
- ord-9b30ada0adf74c4882f80056698956d0
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07132533B2
Reaction notes
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