Triethylamine → 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 1453409Notes

Reaction equation

HRID 1453409 reaction equation
[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([O:21]C)=[O:20])=[CH:17][C:18]=4[N:9]3[CH2:8][CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.N1(C(=O)C)CCNCC1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][C:18]=4[N:9]3[CH2:8][CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][C:18]=4[N:9]3[CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 837951-AcetylpiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68832135methyl 7H-indolo[2,1-a][2]benzazepine-10-carboxylate

Product 2

HCID 666396797H-indolo[2,1-a][2]benzazepine-10-carboxylic acidHCID 685639665H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 7H-indolo[2,1-a][2]benzazepine-10-carboxylate, 13-cyclohexyl, 6-carboxylic acid (830 mg, 2.0 mmol), 1-(piperazin-1-yl)ethanone (310 mg, 2.4 mmol) and triethylamine (0.85 mL) in DMF (8 mL) was added HATU (910 mg, 2.4 mmol). The reaction mixture was stirred at rt for 2 h, diluted with H2O (˜15 mL) and the solids were collected by filtration washed with H2O and dried under vacuum overnight to yield 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-6-[[4-(acetyl)-1-piperazinyl]carbonyl]-, methyl ester (1.19 g, 2.3 mmol, quant.) as a yellow solid. LCMS: m/e 526 (M+H)+, ret time 2.96 min, column B, 3 minute gradient.

Workup

  1. filtrationthe solids were collected by filtration
  2. washwashed with H2O
  3. customdried under vacuum overnight

Sources & evidence

ORD record
ord-47d7c34529314b4fb50066aee4aa2d74
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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