Acetamide → HCID 178432473, compound

HRID 1621483Notes

Reaction equation

HRID 1621483 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2C2CCCCO2)=[C:4]([C:17]2[C:18]([NH:34][C:35]3[CH:36]=[CH:37][C:38]([NH:41]C(=O)C)=[N:39][CH:40]=3)=[N:19][CH:20]=[C:21]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=3)[CH:22]=2)[N:3]=1.[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46].C(N)(=O)C>C(Cl)Cl>[F:48][C:47]([F:50])([F:49])[C:45]([OH:51])=[O:46].[F:48][C:47]([F:50])([F:49])[C:45]([OH:51])=[O:46].[CH3:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([C:17]2[C:18]([NH:34][C:35]3[CH:36]=[CH:37][C:38]([NH2:41])=[N:39][CH:40]=3)=[N:19][CH:20]=[C:21]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=3)[CH:22]=2)[N:3]=1

Participants

5

Reactant 3

HCID 178AcetamideHCID 6422Trifluoroacetic acidHCID 66599984HCID 66599984, compound

Product 1

HCID 178432473HCID 178432473, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(5-(3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)-5-(4-(methylsulfonyl)benzyl)pyridin-2-ylamino)pyridin-2-yl)acetamide (24.5 mg, 0.040 mmol) in DCM (3 mL) was treated with TFA (0.5 mL). The reaction was monitored by LCMS and, upon completion, some hydrolyzed acetamide was also observed. The mixture was concentrated and purified by prep HPLC to give N5-(3-(2-methyl-9H-purin-6-yl)-5-(4-(methylsulfonyl)benzyl)pyridin-2-yl)pyridine-2,5-diamine bis(trifluoroacetate) (3.2 mg, 4.48 μmol, 11.20% yield) followed by N-(5-(3-(2-methyl-9H-purin-6-yl)-5-(4-(methylsulfonyl)benzyl)pyridin-2-ylamino)pyridin-2-yl)acetamide trifluoroacetate (8.4 mg, 0.013 mmol, 32.7% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by prep HPLC

Sources & evidence

ORD record
ord-47a8db3fbf404c27a96011d492ee3fa4
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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