Hydrochloric Acid → 1-Quinazolin-4-yl-piperidine-4-carboxylic acid (2-amino-ethyl)-(4-chlorobenzyl)-amide dihydrochloride

HRID 1192332Notes

Reaction equation

HRID 1192332 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:11]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH2:15][CH2:14]1)=[O:12])(C)(C)C.[ClH:38]>C(Cl)Cl.CCOCC.ClCCCl>[ClH:36].[ClH:38].[NH2:7][CH2:8][CH2:9][N:10]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:11]([CH:13]1[CH2:14][CH2:15][N:16]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH2:17][CH2:18]1)=[O:12]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67539006HCID 67539006, compound

Product 1

HCID 866431541-Quinazolin-4-yl-piperidine-4-carboxylic acid (2-amino-ethyl)-(4-chlorobenzyl)-amide dihydrochloride

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Step 5: 1 {2-[(4-Chlorobenzyl)-(1-quinazolin-4-yl-piperidine-4-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester (190 mg, 0.36 mmol) was dissolved in DCM (5 mL) followed by the addition of 2.0 M HCl in Et2O (2 mL). After being stirred for 12 hours, the mixture was diluted with DCE and concentrated in vacuo. The resulting white solid was then suspended in MeCN and concentrated in vacuo (repeated twice) to give 1-quinazolin-4-yl-piperidine-4-carboxylic acid (2-amino-ethyl)-(4-chlorobenzyl)-amide dihydrochloride as a white powder (120 mg). 1H NMR (DMSO-d6, 400 MHz) δ 8.83 (m, 1H), 8.51 (bs, 2H), 8.20 (m, 2H), 8.01 (m, 2H), 7.71 (m, 1H), 7.48 (d, J=8.3 Hz, 1H), 7.39 (d, J=8.3 Hz, 1H), 7.31 (d, J=8.3 Hz, 1H), 7.25 (d, J=8.3 Hz, 1H), 4.79 (m, 2H), 4.55 (s, 1H), 3.59 (m, 7H), 3.03 (m, 1H), 2.90 (m, 1H), 1.92 (m, 4H). LCMS (APCI+) m/z 424, 426 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. concentrationconcentrated in vacuo (

Sources & evidence

ORD record
ord-08ea4ede51764b3a91ef956a0a8e211f
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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