Hydrochloric Acid → HCID 136397138, compound

HRID 1693002Notes

Reaction equation

HRID 1693002 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[C:4]=1[C:10]1[N:19]=[C:18]([N:20]2[CH2:24][CH2:23][C@@H:22]([NH:25][C:26](=[O:32])[O:27][CH2:28][CH2:29][O:30][CH3:31])[CH2:21]2)[C:17]2[C:12](=[CH:13][C:14]([CH3:33])=[CH:15][CH:16]=2)[N:11]=1>CCOCC.C(Cl)Cl>[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[C:4]=1[C:10]1[N:19]=[C:18]([N:20]2[CH2:24][CH2:23][C@@H:22]([NH:25][C:26](=[O:32])[O:27][CH2:28][CH2:29][O:30][CH3:31])[CH2:21]2)[C:17]2[C:12](=[CH:13][C:14]([CH3:33])=[CH:15][CH:16]=2)[N:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 135771828HCID 135771828, compound

Product 1

HCID 136397138HCID 136397138, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 6344DichloromethaneSolvent

Procedure

A 2.0 M solution of HCl in ether (0.15 mL) was added to solution of (R)-2-methoxyethyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (130 mg, 0.3 mmol) in CH2Cl2 (2 mL) and ether (10 mL). After addition of ether (10 mL), a precipitate formed which was filtered and dried. The material was dissolved in MeOH and dried under reduced pressure to give (R)-2-methoxyethyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (HCl salt of compound 1) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 8.35 (s, 1H), 7.76 (d, J=5.5 Hz, 1H), 7.67 (s, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.47 (m, 1H), 6.99 (d, J=8.3 Hz, 1H), 6.87 (t, J=9.0 Hz, 1H), 4.29 (m, 3H), 3.77-3.36 (m, 5H), 3.23 (s, 3H), 3.06 (m, 1H), 2.56 (s, 3H), 2.23 (s, 1H), 2.06 (s, 1H) ppm. LC/MS: m/z 441.3 (M+H)+ at 2.11 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customa precipitate formed which
  2. filtrationwas filtered
  3. customdried
  4. dissolutionThe material was dissolved in MeOH
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-6156aa0a2696421285494b9fda6c9e55
Source dataset
uspto-grants-2012_04
Patent number
US08158637B2

Reaction notes

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