1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-[4-(1-tert-Butoxycarbonyl-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-2-oxo-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

HRID 1433005Notes

Reaction equation

HRID 1433005 reaction equation
N12CCCN=C1CCCCC2.[C:12]([O:16][C:17]([N:19]1[C:27]2[CH:26]=[CH:25][N:24]=[CH:23][C:22]=2[CH:21]=[C:20]1[CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]#[C:37][C:38]2[CH:39]=[N:40][CH:41]=[CH:42][C:43]=2[NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:31][C:30]1=[O:52])=[O:18])([CH3:15])([CH3:14])[CH3:13]>CC#N>[C:12]([O:16][C:17]([N:19]1[C:27]2[CH:26]=[CH:25][N:24]=[CH:23][C:22]=2[CH:21]=[C:20]1[CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]2[N:44]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C:43]3[CH:42]=[CH:41][N:40]=[CH:39][C:38]=3[CH:37]=2)[CH2:31][C:30]1=[O:52])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54474940HCID 54474940, compound

Product 1

HCID 690284622-[4-(1-tert-Butoxycarbonyl-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-2-oxo-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl esterYield 108.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (42 mg, 0.27 mmol) is added to a suspension containing 2-{4-[3-(4-tert-butoxycarbonylamino-pyridin-3-yl)-prop-2-ynyl]-2-oxo-piperazin-1-ylmethyl}-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (77 mg, 0.14 mmol) in anhydrous CH3CN (10 mL) and the mixture is warmed to 50° C. After 4 h, the reaction mixture is concentrated to dryness and the residue is partitioned between CH2Cl2 (50 mL) and water (50 mL) and the layers are separated. The aqueous layer is extracted twice with CH2Cl2 (25 mL) and the combined organic phase is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to provide 85 mg of the title compound as a crude solid which is used directly without further purification. 1H NMR (300 MHz, CDCl3) δ1.68 (s, 9H), 1.70 (s, 9H), 2.91 (m, 2H), 3.41 (s, 2H), 3.49 (m, 2H), 4.26 (s, 2H), 4.95 (d, J=1.1 Hz, 2H), 6.39 (d, J=0.7 Hz, 1H), (d, J=0.7 Hz, 1H), 7.86 (m, 1H), 8.41 (m, 1H), 8.76 (br s, 1H), 8.82 (br s, 1H) ppm; MS (EI): m/z 561 (M+H).

Workup

  1. concentrationthe reaction mixture is concentrated to dryness
  2. customthe residue is partitioned between CH2Cl2 (50 mL) and water (50 mL)
  3. customthe layers are separated
  4. extractionThe aqueous layer is extracted twice with CH2Cl2 (25 mL)
  5. washthe combined organic phase is washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cfdbf79708f64cb8860961b4cc46e921
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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