Hydrochloric Acid → HCID 136366951, compound

HRID 2062300Notes

Reaction equation

HRID 2062300 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[CH2:24][CH2:23][CH2:22][C@@H:21]([CH2:25][NH:26][C:27](=[O:29])[O-: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].[CH3:32][CH2:33][O:34][CH2:35]C>C(Cl)Cl>[ClH:31].[CH3:35][O:34][CH2:33][CH2:32][N:26]([CH2:25][C@H:21]1[CH2:22][CH2:23][CH2:24][N:19]([C:17]2[C:16]3[C:11](=[CH:12][C:13]([CH3:30])=[CH:14][CH:15]=3)[N:10]=[C:9]([C:3]3[C:4]([OH:8])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[N:18]=2)[CH2:20]1)[C:27](=[O:28])[OH:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 137227865HCID 137227865, compound

Product 1

HCID 136366951HCID 136366951, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((S)-1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate (352 mg, 0.75 mmol) in CH2Cl2 (3 mL) was added dropwise a 2.0 M HCl solution in ether (0.375 mL, 0.75 mmol) under an N2 atmosphere. It was followed by the addition of 20 mL ether which lead to the precipitation of 2-methoxyethyl((S)-1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate hydrochloride (350 mg, 92%) which was then filtered and dried. LC/MS: m/z 469.5 (M+H)+ at 2.29 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 7.97 (d, J=7.9 Hz, 1H), 7.63 (s, 1H), 7.45 (m, 3H), 6.89 (d, J=8.3 Hz, 1H), 6.82 (t, J=9.5 Hz, 1H), 4.54 (s, 1H), 4.03 (d, J=2.7 Hz, 2H), 3.47 (t, J=4.6 Hz, 4H), 3.24 (s, 3H), 2.99 (m, 2H), 2.54 (s, 3H), 1.89 (m, 3H), 1.70 (m, 1H), 1.38 (m, 1H)

Workup

  1. customlead to the precipitation of 2-methoxyethyl((S)-1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate hydrochloride (350 mg, 92%) which
  2. filtrationwas then filtered
  3. customdried

Sources & evidence

ORD record
ord-4bcac0db3aee46568484f228ae146f5a
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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