N-(2-amino-4-(trifluoromethoxy)phenyl)-3-(3-((((3 aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanamide → HCID 178484168, compound

HRID 511697Notes

Reaction equation

HRID 511697 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=O)[CH2:15][CH2:16][CH:17]1[CH2:20][CH:19]([N:21]([CH2:23][C@@H:24]2[C@@H:31]3[C@@H:27]([O:28][C:29]([CH3:33])([CH3:32])[O:30]3)[C@H:26]([N:34]3[CH:42]=[N:41][C:40]4[C:35]3=[N:36][CH:37]=[N:38][C:39]=4[NH2:43])[O:25]2)[CH3:22])[CH2:18]1>CC(O)=O>[CH3:32][C:29]1([CH3:33])[O:30][C@@H:31]2[C@@H:24]([CH2:23][N:21]([CH3:22])[CH:19]3[CH2:18][CH:17]([CH2:16][CH2:15][C:14]4[NH:13][C:3]5[CH:4]=[CH:5][C:6]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:7][C:2]=5[N:1]=4)[CH2:20]3)[O:25][C@@H:26]([N:34]3[CH:42]=[N:41][C:40]4[C:35]3=[N:36][CH:37]=[N:38][C:39]=4[NH2:43])[C@@H:27]2[O:28]1

Participants

3

Reactant 1

HCID 67777193N-(2-amino-4-(trifluoromethoxy)phenyl)-3-(3-((((3 aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanamide

Product 1

HCID 178484168HCID 178484168, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(2-amino-4-(trifluoromethoxy)phenyl)-3-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanamide (1.0 g, 1.61 mmol) in HOAc (10 mL) was stirred at 65° C. overnight. The mixture was cooled to rt and concentrated. The residue was dissolved in DCM (50 mL), washed wth saturation NaHCO3 solution (10 mL×2), water (20 mL) and brine (30 mL). The residue was separated by chiral HPLC to afford the cis isomer (460 mg, yield: 47%) and the trans isomer (220 mg, yield: 23%).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in DCM (50 mL)
  3. washwashed wth saturation NaHCO3 solution (10 mL×2), water (20 mL) and brine (30 mL)
  4. customThe residue was separated by chiral HPLC
  5. customto afford the cis isomer (460 mg, yield: 47%)

Sources & evidence

ORD record
ord-1839d93e4bb84da99de17d589d3b8327
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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