Hydrochloric Acid → HCID 178464479, compound

HRID 2169185Notes

Reaction equation

HRID 2169185 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:29]([N:31]([CH2:38][CH2:39][O:40][Si](C(C)(C)C)(C)C)[CH:32]([CH3:37])[C:33]([F:36])([F:35])[F:34])=[O:30])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([C:29]([N:31]([CH2:38][CH2:39][OH:40])[CH:32]([CH3:37])[C:33]([F:36])([F:35])[F:34])=[O:30])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178464493HCID 178464493, compound

Product 1

HCID 178464479HCID 178464479, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxy-N-(1,1,1-trifluoropropan-2-yl)pyrimidine-4-carboxamide (42) (138 mg, 199 μmol, Eq: 1.00) in tetrahydrofuran (5 ml) was added HCl (1N) (299 μl, 299 μmol, Eq: 1.5) at room temperature and the reaction mixture was stirred for 4 hrs, neutralized with aqueous 1N NaoH solution, extracted with ethyl acetate, dried (MgSO4), concentrated, and chromatographed (silica gel, gradient, 0 to 5% methanol-dichloromethane) to obtain 5-(benzyloxy)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxy-N-(2-hydroxyethyl)-N-(1,1,1-trifluoropropan-2-yl)pyrimidine-4-carboxamide (43) (white foam, 102 mg, 176 μmol, 88.5% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customchromatographed (silica gel, gradient, 0 to 5% methanol-dichloromethane)

Sources & evidence

ORD record
ord-c72874cfcb094038a0f86598d66383c8
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

Loading…