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

HRID 1453352Notes

Reaction equation

HRID 1453352 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(C2N=CC=CN=2)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

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 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 1

HCID 666396797H-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 (150 mg, 0.36 mmol), 2-(piperazin-1-yl)pyrimidine (76 mg, 0.38 mmol) and triethylamine (0.10 mL) in DMF (2 mL) was added HATU (160 mg, 0.42 mmol). The reaction mixture was stirred at rt for 15 min., diluted with H2O (˜4 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-(4-morpholinylcarbonyl)-1-piperazinyl]carbonyl]-, methyl ester (170 mg, 0.30 mmol, 83%) as a yellow solid. 1H NMR (500 MHz, CDCl3) δ 8.15 (s, 1H), 7.88 (d, J=8.5 Hz, 1H), 7.74 (br d, J=8.5 Hz, 1H), 7.58 (br d, J=7.6 Hz, 1H), 7.52-7.44 (m, 2H), 7.39 (br d, J=7.3 Hz, 1H), 6.85 (s, 1H), 5.12(br s, 1H), 4.40 (br s, 1H), 3.94 (s, 3H), 3.72-3.01 (m, 8H), 3.63 (dd, J=4.9, 4.3 Hz, 4H), 3.20 (dd, J=4.9, 4.3 Hz, 4H), 2.88-2.81 (m, 1H), 2.16-1.15 (m, 10H). LCMS: m/e 597 (M+H)+, ret time 1.82 min, column A, 2 minute gradient.

Workup

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

Sources & evidence

ORD record
ord-d2f86121157f4a7894eea1ab9c2f590b
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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