Hydrochloric Acid → HCID 136380819, compound

HRID 1616140Notes

Reaction equation

HRID 1616140 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:31])[NH:10][C:11]([C:15]([NH:17][CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[O:16])=[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:31])[NH:10][C:11]([C:15]([NH:17][CH:18]3[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]3)=[O:16])=[N:12]2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 136390990HCID 136390990, compound

Product 1

HCID 136380819HCID 136380819, 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}carbonyl)amino]piperidine-1-carboxylate (45 mg, 0.1 mmol) in methylene chloride (1.5 mL) was added 4.0 M hydrochloric acid in 1,4-dioxane (1.50 mL, 6.0 mmol). The reaction mixture was stirred at rt for 2 h. The solid was filtered and washed with DCM to afford N7-hydroxy-4-oxo-N2-piperidin-4-yl-3,4-dihydroquinazoline-2,7-dicarboxamide.HCl (34 mg, 89%). LC-MS: (FA) ES+ 332; 1H NMR (300 MHz, DMSO) δ 12.42 (s, 1H), 11.55 (s, 1H), 9.28 (s, 1H), 9.11 (d, J=7.7 Hz, 1H), 8.82 (s, 1H), 8.21 (d, J=8.2 Hz, 1H), 8.17 (s, 1H), 7.91 (d, J=8.0 Hz, 1H), 4.13-3.97 (m, 1H), 3.38-3.27 (m, 2H), 3.09-2.95 (m, 2H), 2.02-1.81 (m, 4H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with DCM

Sources & evidence

ORD record
ord-6621d42540d54731a20819e52c78cdf1
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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