Hydrochloric Acid → HCID 59326831, compound

HRID 410325Notes

Reaction equation

HRID 410325 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-fc009974cf814c17a0c7f1ef45081ebd
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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