Hydrochloric Acid → HCID 136412256, compound

HRID 2079420Notes

Reaction equation

HRID 2079420 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2[N:19]1[CH2:23][CH2:22][C@@H:21]([NH:24][C:25](=[O:32])[O:26][C@H:27]2[CH2:31][CH2:30][O:29][CH2:28]2)[CH2:20]1.C(Cl)[Cl:34].Cl>CCOCC>[ClH:34].[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2[N:19]1[CH2:23][CH2:22][C@@H:21]([NH:24][C:25](=[O:32])[O:26][C@H:27]2[CH2:31][CH2:30][O:29][CH2:28]2)[CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 136121408HCID 136121408, compound

Product 1

HCID 136412256HCID 136412256, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of (S)-tetrahydrofuran-3-yl (R)-1-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)pyrrolidin-3-ylcarbamate (250 mg, 0.57 mmol) and CH2Cl2 (25 mL) was added a 2.0 M HCl solution in ether (0.285 mL, 0.57 mmol). After the addition of ether (40 mL), the reaction was stirred for 1 h. The resulting solid was filtered and dried to afford (S)-tetrahydrofuran-3-yl (R)-1-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride. LC/MS: m/z 439.5 (M+H)+ at 2.25 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.18 (dd, J=8.1, 1.4 Hz, 1H), 8.00 (d, J=9.6 Hz, 1H), 7.90-7.94 (m, 1H), 7.78-7.83 (m, 1H), 7.45-7.49 (m, 1H), 7.00-7.03 (m, 2H), 5.10 (s, 1H), 4.09-4.25 (m, 4H), 3.90-3.92 (m, 1H), 3.62-3.75 (m, 4H), 2.22-2.27 (m, 1H), 2.03-2.14 (m, 2H), 1.83-1.91 (m, 1H) ppm.

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-19d2f79bfd444657865918f5be864c80
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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