Dichloromethane → HCID 86695069, compound

HRID 574344Notes

Reaction equation

HRID 574344 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:7][CH2:6][N:5]([C:8]2[N:13]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:16]=[C:12]3[N:11]=[C:10]([CH3:23])[C:9]=2[CH:24]([OH:29])[C:25]([O:27][CH3:28])=[O:26])[CH2:4][CH2:3]1.[C:31](OC(=O)C)([CH3:34])([CH3:33])[CH3:32].C(Cl)Cl.Cl(O)(=O)(=O)=O>CCOC(C)=O>[C:31]([O:29][CH:24]([C:9]1[C:10]([CH3:23])=[N:11][C:12]2[N:13]([N:14]=[C:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:16]=2)[C:8]=1[N:5]1[CH2:4][CH2:3][C:2]([CH3:30])([CH3:1])[CH2:7][CH2:6]1)[C:25]([O:27][CH3:28])=[O:26])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10908tert-Butyl acetateHCID 24247Perchloric AcidHCID 86695068HCID 86695068, compound

Product 1

HCID 86695069HCID 86695069, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (56 mg, 0.137 mmol) in t-butylacetate (2 ml, 0.137 mmol) was added anhydrous DCM (Volume: 2 ml) followed by perchloric acid (0.012 ml, 0.205 mmol). The resulting mixture was stirred at r.t for 1 h. Diluted with EtOAc, washed with sat'd NaHCO3. The organic phase was dried and evaporated to an oil, which was purified by Pre-HPLC to afford methyl 2-tert-butoxy-2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate (25 mg, 0.053 mmol, 38.5% yield). 1H-NMR (400 MHz, CDCl3) δ 1.16 (6H, s), 1.26 (9H, s), 1.58-1.60 (2H, m), 1.69-1.73 (2H, m), 2.69 (3H, s), 3.77 (3 H, s), 5.87 (1 H, s), 7.49-7.53 (3 H, m), 8.35-8.37 (2 H, m).

Workup

  1. washwashed with sat'd NaHCO3
  2. customThe organic phase was dried
  3. customevaporated to an oil, which
  4. customwas purified by Pre-HPLC

Sources & evidence

ORD record
ord-966a8dcd88c141a4b93529f59fcd12ac
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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