Hydrochloric Acid → HCID 136406834, compound

HRID 2406187Notes

Reaction equation

HRID 2406187 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9]1[N:18]=[C:17]([N:19]2[CH2:23][CH2:22][C@@H:21]([NH:24][C:25](=[O:32])[O:26][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:33])=[CH:14][CH:15]=2)[N:10]=1.[ClH:34].CCOCC>C(Cl)Cl>[ClH:34].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9]1[N:18]=[C:17]([N:19]2[CH2:23][CH2:22][C@@H:21]([NH:24][C:25](=[O:32])[O:26][CH2:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:33])=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 135771841HCID 135771841, compound

Product 1

HCID 136406834HCID 136406834, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-neopentyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (224 mg, 0.49 mmol) in CH2Cl2 (5 mL) was added a 2.0 M solution of HCl in ether (0.24 mL, 0.49 mmol). After the addition of ether (20 mL), a precipitate formed, which was filtered and dried under vacuum to give (R)-neopentyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (HCl salt of compound 13) (225 mg, 94%). 1H NMR (400 MHz, DMSO-d6). LC/MS: m/z 453.3 (M+H)+ at 2.73 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customa precipitate formed
  2. filtrationwhich was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-199d707c2b5744df8f35cff518439f62
Source dataset
uspto-grants-2014_08
Patent number
US08809353B2

Reaction notes

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