Hydrochloric Acid → HCID 58764149, compound

HRID 1438324Notes

Reaction equation

HRID 1438324 reaction equation
[CH:1]1([C:6]2([CH2:26][CH2:27][CH2:28][CH2:29][CH:30]3[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]3)[CH2:11][C:10]([OH:12])=[C:9]([CH2:13][C:14]3[N:24]=[C:17]4[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]4[N:15]=3)[C:8](=[O:25])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCOCC1>[CH:1]1([C:6]2([CH2:26][CH2:27][CH2:28][CH2:29][CH:30]3[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]3)[O:7][C:8](=[O:25])[C:9]([CH2:13][C:14]3[N:24]=[C:17]4[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]4[N:15]=3)=[C:10]([OH:12])[CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57956281HCID 57956281, compound

Product 1

HCID 58764149HCID 58764149, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl 4-(4-{2-cyclopentyl-5-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}butyl)piperidine-1-carboxylate (example B(41)) (0.47 g, 0.8 mmol) was dissolved in dioxane (1 mL) and 4N HCl in dioxane (1 mL). The reaction was stirred overnight at room temperature. Solvents were removed and the residue was purified using a Dionex system (30-70% CH3CN/H2O (0.1% ACOH). 1H NMR (400 MHz, DMSO-d6): δ 1.37-1.70 (m, 20H), 2.63-2.85 (m, 12H), 3.69-3.95 (m, 4H), 7.98 (s, 1H), 11.12 (s, 1H). Anal. Calcd. For C27H39N5O3.1.0HCl. 1.5H2O: C, 59.49; H, 7.95; N, 12.85. Found: C, 59.60; H, 8.04; N, 12.95. ESIMS (MH+): 482.

Workup

  1. customSolvents were removed
  2. customthe residue was purified

Sources & evidence

ORD record
ord-507b6d99266f4d8fbcd6d566f667f315
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

Loading…