Triethylamine → HCID 69060367, compound

HRID 1821597Notes

Reaction equation

HRID 1821597 reaction equation
[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[N:11]([CH2:22][OH:23])[N:12]=[C:13]([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[F:21])[C:8]2=[C:7]([NH:24][CH2:25][CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[N:6]=1.[C:36]([NH:43][C@H:44]([C:48](O)=[O:49])[CH:45]([CH3:47])[CH3:46])([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.ClC(OC(C)=C)=O>C(Cl)Cl>[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[N:11]([CH2:22][O:23][C:48](=[O:49])[CH:44]([NH:43][C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH:45]([CH3:47])[CH3:46])[N:12]=[C:13]([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[F:21])[C:8]2=[C:7]([NH:24][CH2:25][CH2:26][S:27]([CH3:30])(=[O:28])=[O:29])[N:6]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 83693Boc-L-ValineHCID 93846Isopropenyl chloroformateHCID 16117146HCID 16117146, compound

Product 1

HCID 69060367HCID 69060367, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[6-(2,4-Difluoro-phenoxy)-3-(2,5-difluoro-phenyl)-4-(2-methanesulfonyl-ethylamino)-pyrazolo[3,4-d]pyrimidin-1-yl]-methanol (170 mg, 0.33 mmol) was dissolved in methylene chloride, and Boc-(L)-Valine (216 mg, 0.99 mmol), dimethylamino pyridine (81 mg, 0.66 mmol), and triethylamine (0.23 mL, 1.6 mmol) were added. The reaction mixture was cooled to 0° C. and stirred under nitrogen, and isopropenyl chloroformate (54 uL, 0.49 mmol) was added. The reaction mixture was stirred for 10 minutes and then partitioned between water and methylene chloride. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography through silica (1:1 hexanes/EtOAc) to give 120 mg of 2-tert-butoxycarbonylamino-3-methyl-butyric acid 6-(2,4-difluoro-phenoxy)-3-(2,5-difluoro-phenyl)-4-(2-methanesulfonyl-ethylamino)-pyrazolo[3,4-d]pyrimidin-1-ylmethyl ester as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 10 minutes
  2. custompartitioned between water and methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography through silica (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-83307cd99db84c60ab6e5cff4c841983
Source dataset
uspto-grants-2009_10
Patent number
US07608603B2

Reaction notes

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