Hydrochloric Acid → HCID 136380814, compound

HRID 1616121Notes

Reaction equation

HRID 1616121 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:30])[NH:10][C:11]([CH2:15][NH:16][CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)=[N:12]2)=[CH:7][CH:6]=1)=[O:4].Cl.O1CCOCC1>C(Cl)Cl>[OH:1][NH:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:30])[NH:10][C:11]([CH2:15][NH:16][CH:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)=[N:12]2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 136078992HCID 136078992, compound

Product 1

HCID 136380814HCID 136380814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[({7-[(hydroxyamino)carbonyl]-4-oxo-3,4-dihydroquinazolin-2-yl}methyl)amino]piperidine-1-carboxylate, 1-56 (98 mg, 0.23 mmol) in methylene chloride (3.2 mL) was added 4.0 M hydrochloric acid in 1,4-dioxane (3.2 mL, 12.8 mmol). The reaction mixture was stirred at rt for 2 h. The solid was filtered and washed with DCM to afford N-hydroxy-4-oxo-2-[(piperidin-4-ylamino)methyl]-3,4-dihydroquinazoline-7-carboxamide.2[HCl] (44 mg, 48%). LC-MS: (FA) ES+ 318; 1H NMR (300 MHz, DMSO) δ 12.80 (s, 1H), 11.63 (s, 1H), 10.04 (s, 1H), 9.48-9.28 (m, 1H), 9.07 (s, 1H), 8.18 (d, J=8.3 Hz, 1H), 8.07 (d, J=1.2 Hz, 1H), 7.88 (dd, J=8.3, 1.5 Hz, 1H), 4.28 (s, 2H), 3.45-3.26 (m, 3H), 3.02-2.84 (m, 2H), 2.34-2.20 (m, 2H), 2.11-1.88 (m, 2H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with DCM

Sources & evidence

ORD record
ord-8188a4527c9b42ad85bfe2f0259f846c
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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