Hydrochloric Acid → HCID 68682260, compound

HRID 1713811Notes

Reaction equation

HRID 1713811 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([NH:20][C:21](=[O:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:27]>O1CCOCC1>[ClH:27].[CH3:25][O:24][C:22](=[O:23])[C:21]([NH:20][C:17]1[CH:16]=[N:15][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:19][CH:18]=1)=[O:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69406367HCID 69406367, compound2×

Product 1

HCID 68682260HCID 68682260, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-Butyl-4-(5-{[methoxy(oxo)acetyl]amino}pyrimidin-2-yl)piperazine 1-carboxylate (Intermediate 53; 4.14 g, 11.33 mmol) in a 4M solution of HCl in dioxane (40 mL) was stirred for 16 h. The precipitate was collected by filtration and washed with ether to give N-(5-{[methoxy(oxo)acetyl]amino}pyrimidin-2-yl)piperazine hydrochloride as a solid. Pyridine (9.16 mL, 113.30 mmol), followed by acetyl chloride (0.97 mL, 13.60 mmol) were added to an ice-cooled suspension of this solid (3.4 g) in DCM (100 mL) and the mixture was allowed to warm to ambient temperature and stirred for 1 h. Water (100 mL) was added and the mixture was extracted with DCM (3×100 mL). The organic extracts were combined, dried and concentrated by evaporation. The residue was triturated with isohexane to give the title compound (2.45 g, 70%) as a solid; 1H NMR δ: 10.79 (1H, s), 8.65 (2H, s), 3.84 (3H, s), 3.75-3.65 (4H, m), 3.52-3.45 (4H, m), 2.04 (3H, s); MS m/e MH+: 308.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ether

Sources & evidence

ORD record
ord-820c34608d9e47f69643bd6b7a39a85e
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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