Diethyl Ether → HCID 136412257, compound

HRID 2079424Notes

Reaction equation

HRID 2079424 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][C@H:27]3[CH2:31][CH2:30][O:29][CH2:28]3)[CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:33])=[CH:14][CH:15]=2)[N:10]=1.CCOCC.C(Cl)[Cl:40]>>[ClH:40].[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][C@H:27]3[CH2:31][CH2:30][O:29][CH2:28]3)[CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:33])=[CH:14][CH:15]=2)[N:10]=1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 6344DichloromethaneHCID 136121462HCID 136121462, compound

Product 1

HCID 136412257HCID 136412257, compoundYield 76%

Procedure

To a solution of (S)-tetrahydrofuran-3-yl (R)-1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (160 mg, 0.35 mmol) in 2 mL CH2Cl2 was added 2 M HCL solution in ether (0.176 mL, 0.35 mmol) resulting in precipitation of a solid. After the addition of 10 mL ether, the reaction was stirred for 30 minutes, filtered and the resulting solid was dried to obtain (S)-tetrahydrofuran-3-yl (R)-1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (130 mg, 76%)). LC/MS: m/z 453.3 (M+H)+ at 2.13 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.29 (s, 1H), 7.57 (s, 2H), 7.43-7.49 (m, 1H), 6.83-6.89 (m, 2H), 5.08 (s, 1H), 4.23-4.42 (m, 4H), 3.62-3.73 (m, 5H), 2.24-2.34 (m, 1H), 2.04-2.11 (m, 2H), 1.86-1.92 (m, 1H) ppm.

Workup

  1. customresulting in precipitation of a solid
  2. filtrationfiltered
  3. customthe resulting solid was dried

Sources & evidence

ORD record
ord-b5f6e990bab44c01b3263c4765d8d774
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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