1,2-Dichloroethane → N-[(1S)-1-({(1S,4S)-5-[(5-bromo-2-pyridinyl)carbonyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)-2,2-dimethylpropyl]-1H-indole-2-carboxamide

HRID 2098467Notes

Reaction equation

HRID 2098467 reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([C@@H:10]([NH:15][C:16]([C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[Br:27][C:28]1[CH:29]=[CH:30][C:31]([C:34](O)=[O:35])=[N:32][CH:33]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[Br:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([N:5]2[CH2:6][C@@H:1]3[CH2:7][C@H:4]2[CH2:3][N:2]3[C:8]([C@@H:10]([NH:15][C:16]([C:18]2[NH:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:35])=[N:32][CH:33]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 6085445-Bromopyridine-2-carboxylic acidHCID 67072627N-{(1S)-1-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylcarbonyl]-2,2-dimethylpropyl}-1H-indole-2-carboxamide

Product 1

HCID 67072574N-[(1S)-1-({(1S,4S)-5-[(5-bromo-2-pyridinyl)carbonyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)-2,2-dimethylpropyl]-1H-indole-2-carboxamideYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-{(1S)-1-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylcarbonyl]-2,2-dimethylpropyl}-1H-indole-2-carboxamide (5 g, 14.11 mmol), 5-bromo-2-pyridinecarboxylic acid (2.85 g, 14.11 mmol), EDC (2.7 g, 14.11 mmol), HOBt (1.91 g, 14.11 mmol), NMM (2.14 g, 21.14 mmol) in CH2Cl2 (50 mL) was stirred at room temperature for 12 h. The reaction was diluted with water. The two layers were separated and the organic washed with sat. NaHCO3 and 1N HCl. The resulting organic solution was dried over anhydrous Na2SO4 and concentrated to give the title compound (7 g) as a yellow solid. LCMS (m/z): 540.2 (M+H).

Workup

  1. customThe two layers were separated
  2. washthe organic washed with sat. NaHCO3 and 1N HCl
  3. dry with materialThe resulting organic solution was dried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-565b1c5f6fc64b9f8b813244714698b4
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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