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

HRID 720129

Reaction equation

HRID 720129 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]1([CH3:41])[CH:27]=[CH:26][C:25]([S:28]([NH:31][C:32]2[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=2[C:34](O)=[O:35])(=[O:30])=[O:29])=[CH:24][CH: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:34](=[O:35])[C:33]3[CH:37]=[CH:38][CH:39]=[CH:40][C:32]=3[NH:31][S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:41])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[CH:3]=2)[CH:17]=[N:18][NH:19]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 22763Benzoic acid, 2-(((4-methylphenyl)sulfonyl)amino)-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-one

Product 1

HCID 135774076n-(6-Oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-2-(toluene-4-sulfonylamino)-benzamideYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation of example 122 from the title compound of Example 7 (100 mg, 0.362 mmol), 2-(toluene-4-sulfonylamino)-benzoic acid (158 mg, 0.542 mmol), triethylamine (0.201 mL, 1.446 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (206 mg, 0.542 mmol) in N,N-dimethylformamide (4.0 mL) was carried out analogously to Example 11. When the reaction was judged complete, N,N-dimethylformamide was evaporated and methanol was added. The mixture was filtered and the solids collected and washed with methanol, dichloromethane and diethyl ether. After drying under vacuum, the title compound (121 mg, 0.220 mmol) was obtained as a yellow powder in 61% yield.

Workup

  1. customN,N-dimethylformamide was evaporated
  2. additionmethanol was added
  3. filtrationThe mixture was filtered
  4. customthe solids collected
  5. washwashed with methanol, dichloromethane and diethyl ether
  6. customAfter drying under vacuum

Sources & evidence

ORD record
ord-3a99aa7acb6c4af48342fbebff6a52ee
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Linked notes

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