Diisopropylethylamine → HCID 59511221, compound

HRID 1157286Notes

Reaction equation

HRID 1157286 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]2[C:10]([C:11](=[O:15])[C:12]([OH:14])=O)=[CH:9][NH:8][C:7]=12.[C:18]1([N:24]2[C:28]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[N:27][N:26]=[N:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]2[C:10]([C:11](=[O:15])[C:12]([N:32]3[CH2:33][CH2:34][N:29]([C:28]4[N:24]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[N:25]=[N:26][N:27]=4)[CH2:30][CH2:31]3)=[O:14])=[CH:9][NH:8][C:7]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 38255781-(1-Phenyl-1H-tetrazol-5-YL)piperazineHCID 224762562-(7-chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

Product 1

HCID 59511221HCID 59511221, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(7-chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (5.3 g, 20.8 mmol) (prepared as described on US20050090522A1) in DMF (100 mL) was added 1-(1-phenyl-1H-tetrazol-5-yl)piperazine (4.8 g, 20.8 mmol), TBTU (7.4 g, 23.0 mmol), and N,N-diisopropylethylamine (12.0 mL, 68.9 mmol). The mixture was stirred at rt for 16 hr. The solvent was removed under reduced pressure, and the remaining residue was dissolved in hot MeOH. Upon cooling, precipitate formed. The precipitate was collected by filtration, and was washed with H2O (3×75 mL). The mother liquor was concentrated under reduced pressure, then subjected to a second crystallization using the same method. The combined precipitates gave 1-(7-chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione as a light brown solid (7.3 g, 15.6 mmol). 1H NMR (500 MHz, CDCl3) δ 9.64 (s, 1H), 8.11 (s, 1H), 7.76 (s, 1H), 7.62-7.50 (m, 5H), 4.00 (s, 3H), 3.83-3.81 (m, 2H), 3.57-3.56 (m, 2H), 3.43-3.41 (m, 2H), 3.33-3.32 (m, 2H). LCMS: m/e 467.3 (M+H)+, ret time 1.99 min (method 2).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe remaining residue was dissolved in hot MeOH
  3. temperatureUpon cooling
  4. filtrationThe precipitate was collected by filtration
  5. washwas washed with H2O (3×75 mL)
  6. concentrationThe mother liquor was concentrated under reduced pressure
  7. customsubjected to a second crystallization
  8. customThe combined precipitates

Sources & evidence

ORD record
ord-66d6eab15e114f5bbc28cb7c90b69a74
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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