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

HRID 1453349Notes

Reaction equation

HRID 1453349 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 (63 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-(2-pyrimidinyl)-1-piperazinyl]carbonyl]-, methyl ester (168 mg, 0.30 mmol, 83%) as a yellow solid. 1H NMR (500 MHz, CDCl3) δ 8.28 (d, J=4.9 Hz, 2H), 8.16 (br s, 1H), 7.89 (d, J =8.6 Hz, 1H), 7.74 (dd, J=8.6 Hz, 1H), 7.59 (dd, J=7.6, 1.5 Hz, 1H), 7.52-7.45 (m, 2H), 7.40 (dd, J=7.3, 1.5 Hz, 1H), 7.25 (s, 1H), 6.51 (t, J=4.9 Hz, 1H), 5.15 (br s, 1H), 4.43(br s, 1H), 3.91 (s, 3H), 3.80-3.29 (m, 8H), 2.91-2.82 (m, 1H), 2.17-1.14 (m, 10H). LCMS: m/e 562 (M+H)+, ret time 2.07 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-376030d696a54922bdf60a1d743b64c1
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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