Hydrochloric Acid → HCID 59326831, compound

HRID 1880190Notes

Reaction equation

HRID 1880190 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:37]=[CH:36][C:15]([O:16][C:17]2[C:22]([C:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH:24]=3)=[CH:21][N:20]=[CH:19][N:18]=2)=[CH:14][CH:13]=1)=[O:11].Cl>C(O)=O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:37]=[CH:36][C:15]([O:16][C:17]2[C:22]([C:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH:24]=3)=[CH:21][N:20]=[CH:19][N:18]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59327063HCID 59327063, compound

Product 1

HCID 59326831HCID 59326831, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a round bottom was added tert-butyl 4-(4-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (500 mg, 1.005 mmol), formic acid (10 ml), and hydrochloric acid, 5.0N (0.256 ml, 7.03 mmol) with stirring. The reaction was quenched after 15 minutes with saturated aqueous sodium bicarbonate and extracted with dichloromethane before drying over sodium sulfate, filtering, and concentrating under reduced pressure, affording (1H-benzo[d]imidazol-2-yl)(4-(5-(1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-4-yloxy)phenyl)methanone as a pale yellow solid. IC50 (uM) +++++.

Workup

  1. customThe reaction was quenched after 15 minutes with saturated aqueous sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. dry with materialbefore drying over sodium sulfate
  4. filtrationfiltering
  5. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-e9e528957451470aaae9a962a4454ff6
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

Loading…