Hydrochloric Acid → HCID 9948722, compound

HRID 1433049Notes

Reaction equation

HRID 1433049 reaction equation
C(OC([N:8]1[CH2:13][CH:12]([CH3:14])[N:11]([CH2:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([NH2:26])=[N:21][CH:22]=[N:23]3)=[CH:18][CH:17]=2)[C:10](=[O:27])[CH:9]1[CH2:28][CH2:29][CH3:30])=O)(C)(C)C.Cl>CCOC(C)=O>[NH2:26][C:20]1[C:19]2[C:24](=[CH:25][C:16]([CH2:15][N:11]3[CH:12]([CH3:14])[CH2:13][NH:8][CH:9]([CH2:28][CH2:29][CH3:30])[C:10]3=[O:27])=[CH:17][CH:18]=2)[N:23]=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69024268HCID 69024268, compound

Product 1

HCID 9948722HCID 9948722, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[4-amino-quinazolin-7-ylmethyl]-5-methyl-3-oxo-2-propyl-piperazine-1-carboxylic acid tert-butyl-ester (0.91 g, 2.2 mmol) in EtOAc (40 mL) is bubbled HCl (gas) for 5 min. at 0° C. After this time, the solution is stirred at ambient temperatures for 15 min. The solution is concentrated. The residue is purified by column chromatography eluting with 1:5:100 NH4OH/MeOH/CH2Cl2. The title compound (0.5 g) is obtained as a white solid. 1H NMR (300 MHz, CDOD) δ8.40 (s, 1H), 8.04 (d, 1H), 7.52 (s, 1H), 7.36 (m, 1H), 5.10 (d, 1H), 4.45 (d, 1H), 3.55 (m, 2H), 3.10 (m, 1H), 2.81 (m, 1H), 1.90 (m, 1H), 1.72 (m, 1H), 1.44 (m, 2H), 1.29 (d, 3H), 0.96 (m, 3H).

Workup

  1. concentrationThe solution is concentrated
  2. customThe residue is purified by column chromatography
  3. washeluting with 1:5:100 NH4OH/MeOH/CH2Cl2

Sources & evidence

ORD record
ord-35e9ce479ed9424caad842946491338a
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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