1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178429879, compound

HRID 15924Notes

Reaction equation

HRID 15924 reaction equation
C1CCN2C(=NCCC2)CC1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:21]([C:29]3[N:33](CCC#N)[N:32]=[N:31][N:30]=3)=[CH:22][N:23]([CH3:28])[C:24](=[O:27])[C:25]=2[CH3:26])=[C:15]([F:38])[CH:14]=1>C(Cl)Cl.C(OCC)(=O)C>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:21]([C:29]3[NH:33][N:32]=[N:31][N:30]=3)=[CH:22][N:23]([CH3:28])[C:24](=[O:27])[C:25]=2[CH3:26])=[C:15]([F:38])[CH:14]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 666744343-{5-[4-(4-Bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl]-tetrazol-1-yl}-propionitrile

Product 1

HCID 178429879HCID 178429879, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

DBU (0.030 mL, 0.21 mmol) was added to a solution of 3-{5-[4-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl]-tetrazol-1-yl}-propionitrile (30 mg, 0.069 mmol) in methylene chloride (1.5 mL). After 2 hours, the reaction mixture was diluted with ethyl acetate and washed with 1 N HCl. The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure. Trituration with diethyl ether gave clean desired product (20 mg, 77%); MS APCI (−) m/z 377, 379 (M−, Br pattern) detected; 1H NMR (400 MHz, CD3OD) δ 8.20 (s, 1H), 7.29 (dd, 1H), 7.13 (dd, 1H), 6.63 (t, 1H), 3.65 (s, 3H), 1.91 (s, 3H).

Workup

  1. washwashed with 1 N HCl
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1230f8d5bbb49cfad6eeedb953150a5
Source dataset
uspto-grants-2010_06
Patent number
US07732616B2

Reaction notes

Loading…