Sulfuric Acid → HCID 136366722, compound

HRID 2062248Notes

Reaction equation

HRID 2062248 reaction equation
[OH:1][C@H:2]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[N:14]=[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[OH:28])[N:12]=2)[CH2:7][CH2:6]1)=[O:4].C1COCC1.[OH:38][S:39]([OH:42])(=[O:41])=[O:40]>CC#N>[S:39]([OH:42])([OH:41])(=[O:40])=[O:38].[OH:1][C@H:2]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[N:14]=[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[OH:28])[N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 135461071HCID 135461071, compound

Product 1

HCID 136366722HCID 136366722, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring yellow solution of (R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-4-methylpentan-1-one (200 mg, 0.46 mmol) and THF (0.9 mL) under an N2 atmosphere was added a solution of concentrated H2SO4 solution (95.9%) (26 μL, 0.46 mmol) and CH3CN (0.75 mL) in a single portion. A white precipitate formed slowly over a period of 1 h. The solid was filtered and vacuum dried to obtain (R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-4-methylpentan-1-one sulfate as a white solid (229 mg, 94%). LC/MS: m/z 435.3 (M+H)+ at 2.81 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.20 (dd, J=7.9, 1.5 Hz, 1H), 8.12 (d, J=8.6 Hz, 1H), 7.77 (s, 1H), 7.53-7.49 (m, 2H), 7.10-7.03 (m, 2H), 4.39-4.35 (m, 1H), 4.30-4.04 (m, 4H), 3.93-3.69 (m, 4H), 2.55 (s, 3H), 1.86-1.73 (m, 1H), 1.52-1.33 (m, 2H), 0.93-0.91 (m, 6H).

Workup

  1. customA white precipitate formed slowly over a period of 1 h
  2. filtrationThe solid was filtered
  3. customvacuum dried

Sources & evidence

ORD record
ord-91a4afadc69146b3ac20299ca4f1fa8a
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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