Hydrochloric Acid → 2-{6-[3(R)-Amino-piperidin-1-yl]-5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl}-benzonitrile

HRID 505903Notes

Reaction equation

HRID 505903 reaction equation
C(O)(=O)C1C=CC=CC=1.[NH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]2[N:22]([CH2:23][C:24]3[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=3[C:26]#[N:27])[C:21](=[O:32])[N:20](C)[C:19](=[O:34])[CH:18]=2)[CH2:12]1.[ClH:35]>C1COCC1.O1CCOCC1>[NH2:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]2[N:22]([CH2:23][C:24]3[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=3[C:26]#[N:27])[C:21](=[O:32])[NH:20][C:19](=[O:34])[C:18]=2[Cl:35])[CH2:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 666977522-[[6-(3-Aminopiperidin-1-yl)-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile;benzoic acid

Product 1

HCID 112105882-{6-[3(R)-Amino-piperidin-1-yl]-5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl}-benzonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 4 (100 mg) in THF (2 mL) was treated with 4M HCl in dioxane (1 mL) at rt for 1 h, concentrated, and then purified by LC-MS to give the title compound. 1H-NMR (400 MHz, DMSO-D6): δ ppm 12.0 (s, 1H), 7.88 (d, J=7.6 Hz, 1H), 7.68 (t, J=7.7 Hz, 1H), 7.49 (t, J=7.7 Hz, 1H), 7.36 (d, J=7.8 Hz, 1H), 5.09-5.21 (m, 2H), 3.17 (m, 2H), 2.96 (t, J=11.1 Hz, 1H), 2.86 (d, J=10.6 Hz, 1H), 2.65 (m, 1H), 1.90 (d, J=11.6 Hz, 1H), 1.57 (d, J=13.1 Hz, 1H), 1.19-1.31 (m, 1H), 1.03-1.15 (m, 1H). MS (ES) [m+H] calc'd for C17H19ClN5O2, 360.1; found, 360.1.

Workup

  1. concentrationconcentrated
  2. custompurified by LC-MS

Sources & evidence

ORD record
ord-74192c345a5d4ed4986e1acd3107cef3
Source dataset
uspto-grants-2010_08
Patent number
US07781584B2

Reaction notes

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