HCID 67818475, compound → HCID 178491021, compound

HRID 2284555Notes

Reaction equation

HRID 2284555 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:22][C@@H:23]1[C@@H:30]2[C@@H:26]([O:27][C:28]([CH3:32])([CH3:31])[O:29]2)[C@H:25]([N:33]2[C:37]3[N:38]=[CH:39][N:40]=[C:41]([NH:42][CH2:43][C:44]4[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][C:45]=4[O:52][CH3:53])[C:36]=3[CH:35]=[CH:34]2)[O:24]1)[CH:19]([CH3:21])[CH3:20]>C(O)(=O)C>[C:8]([C:6]1[CH:5]=[CH:4][C:3]2[NH:12][C:13]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:22][C@@H:23]3[C@H:30]4[O:29][C:28]([CH3:31])([CH3:32])[O:27][C@H:26]4[C@H:25]([N:33]4[C:37]5[N:38]=[CH:39][N:40]=[C:41]([NH:42][CH2:43][C:44]6[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][C:45]=6[O:52][CH3:53])[C:36]=5[CH:35]=[CH:34]4)[O:24]3)[CH:19]([CH3:21])[CH3:20])=[N:1][C:2]=2[CH:7]=1)([CH3:9])([CH3:11])[CH3:10]

Participants

3

Reactant 1

HCID 67818475HCID 67818475, compound

Product 1

HCID 178491021HCID 178491021, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

N-(2-amino-4-(tert-butyl)phenyl)-5-((((3aR,4R,6R,6aR)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(isopropyl)amino)pentanamide (140 mg, mmol) was taken up in acetic acid (3.5 mL) and the solution was heated at 65° C. for 2 h, whereupon HPLC indicated the starting material had been consumed. The reaction mixture was cooled to room temperature and the solvent was removed under high vac. The residue was taken up in 30 mL CH2Cl2 and washed with 20 mL portions of sat NaHCO3 and 2% Na2CO3 solution. The organic phase was dried over Na2SO4, filtered and concentrated to yield a light tan glass/stiff foam. The crude material was purified by flash chromatography (25 g silica gel; 3% 7N NH3 in CH3OH/CH2Cl2) to yield the title compound (120 mg, 88%) as a slightly tan glass: MS (ESI+) for C41H55N7O5 m/z 726.5 (M+H)+; MS (ESI−) for C41H55N7O5 m/z 724.6 (M−H)−; HPLC purity 90% (ret. time, 3.14 min).

Workup

  1. customhad been consumed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solvent was removed under high vac
  4. washwashed with 20 mL portions of sat NaHCO3 and 2% Na2CO3 solution
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a light tan glass/stiff foam
  9. customThe crude material was purified by flash chromatography (25 g silica gel; 3% 7N NH3 in CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-54f4165ccd1c4a7f93af5532f35a10c4
Source dataset
uspto-grants-2015_09
Patent number
US09145438B2

Reaction notes

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