Triethylamine → n-(6-Oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-2-tetrazol-1-yl-acetamide

HRID 720072Notes

Reaction equation

HRID 720072 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.[N:22]1([CH2:27][C:28](O)=[O:29])[CH:26]=[N:25][N:24]=[N:23]1.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>CN(C)C=O>[O:21]=[C:20]1[C:4]2[C:5]3[C:6](=[C:7]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:8][C:9]=3[CH:10]=[C:2]([NH:1][C:28](=[O:29])[CH2:27][N:22]3[CH:26]=[N:25][N:24]=[N:23]3)[CH:3]=2)[CH:17]=[N:18][NH:19]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5432071-Tetrazolylacetic acid2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 1357740798-Amino-2-phenyl-1,5-dihydro-[1,2]diazepino[4,5,6-cd]indol-6-one

Product 1

HCID 135546089n-(6-Oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-2-tetrazol-1-yl-acetamideYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation of example 12 from the title compound of Example 7 (15 mg, 0.054 mmol), tetrazol-1-yl-acetic acid (8 mg, 0.062 mmol), triethylamine (0.030 mL, 0.22 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (25 mg, 0.065 mmol) in N,N-dimethylformamide (1.0 mL) was carried out analogously to Example 11. Additional tetrazol-1-yl-acetic acid acid (1.0 mg, 0.008 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.0 mg, 0.008 mmol) were added after c.a. 18 hours to drive the reaction to completion. Filtration, concentration and recrystallization afforded the title compound (12 mg, 0.031 mmol) as a yellow powder in 58% yield.

Workup

  1. custom18 hours
  2. customthe reaction to completion
  3. filtrationFiltration, concentration and recrystallization

Sources & evidence

ORD record
ord-0826e090eebc4f6d90e372e09c944945
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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