Hydrochloric Acid → HCID 136406833, compound

HRID 2406185Notes

Reaction equation

HRID 2406185 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:29])[O:26][CH2:27][CH3:28])[CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:30])=[CH:14][CH:15]=2)[N:10]=1.[ClH:31]>C(Cl)Cl.CCOCC>[ClH:31].[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:29])[O:26][CH2:27][CH3:28])[CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:30])=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 135771836HCID 135771836, compound

Product 1

HCID 136406833HCID 136406833, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-ethyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (129 mg, 0.31 mmol) in CH2Cl2 (10 mL) was added a 2.0 M solution of HCl in ether (0.155 mL). After the addition of ether (28 mL), a precipitate formed, and the mixture was stirred for 30 minutes. The solid was filtered and dried under high vacuum to give (R)-ethyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (HCl salt of compound 10) (140 mg, 100%). 1H NMR (400 MHz, DMSO-d6) δ 8.36 (s, 1H), 7.64-7.58 (m, 3H), 7.47 (q, J=7.8 Hz, 1H), 6.96 (d, J=8.3 Hz, 1H), 6.87 (t, J=9.1 Hz, 1H), 4.26 (s, 2H), 4.03-3.98 (m, 4H), 3.38-3.36 (m, 1H, broad due to water), 2.56 (s, 3H), 2.23 (s, 1H), 2.04 (s, 1H), 1.16 (t, J=7.1 Hz, 3H) ppm. LC/MS: m/z 411.1 (M+H)+ at 2.25 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customa precipitate formed
  2. filtrationThe solid was filtered
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-5da78bbc57c34cb38d0ed651b4607101
Source dataset
uspto-grants-2014_08
Patent number
US08809353B2

Reaction notes

Loading…