Potassium Carbonate → HCID 178505954, compound

HRID 1950750Notes

Reaction equation

HRID 1950750 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][NH:15]3)=[C:11]([N:18]3[CH2:24][CH2:23][C:22]4[N:25]=[CH:26][NH:27][C:21]=4[CH2:20][CH2:19]3)[N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.ClC1N=C2C(N=CN2)=C(N2CCC3N=CNC=3C2)N=1.NC1C=CC(NC2CCN(C(OC(C)(C)C)=O)CC2)=C(F)C=1.[F:76][C:77]([F:88])([F:87])[CH2:78]OS(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[CH:14][NH:15]3)=[C:11]([N:18]3[CH2:19][CH2:20][C:21]4[N:27]=[CH:26][NH:25][C:22]=4[CH2:23][CH2:24]3)[N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:28][CH:29]1[CH2:34][CH2:33][N:32]([CH2:78][C:77]([F:88])([F:87])[F:76])[CH2:31][CH2:30]1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 68671753HCID 68671753, compoundHCID 178478371HCID 178478371, compoundHCID 178505953HCID 178505953, compound

Product 1

HCID 178505954HCID 178505954, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

40 mg of 2-fluoro-N1-piperidin-4-yl-N4-[6-(4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepin-6-yl)-9H-purin-2-yl]-benzene-1,4-diamine (prepared analogously to Example 1 from 2-chloro-6-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)-9H-purine and tert-butyl 4-(4-amino-2-fluoro-phenylamino)-piperidine-1-carboxylate), 12.86 μL of 2,2,2-trifluoroethyl-trifluoromethylsulphonate and 61.63 mg potassium carbonate are suspended in N,N-dimethylformamide and stirred for 2 h at 25° C. The reaction mixture is filtered to remove the insoluble constituents and the filtrate is purified by column chromatography. The carrier material used is C18-RP silica gel and the product is passed through a gradient that consists of 85% water and 15% acetonitrile at the starting point and 5% water and 95% acetonitrile at the finishing point. 0.2% NH3KHCO3 is added to both eluants. The suitable fractions are freeze-dried.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove the insoluble constituents
  3. customthe filtrate is purified by column chromatography
  4. addition0.2% NH3KHCO3 is added to both eluants
  5. customThe suitable fractions are freeze-dried

Sources & evidence

ORD record
ord-60b9854f40714775a7ecadf139dcd9c0
Source dataset
uspto-grants-2013_03
Patent number
US08404674B2

Reaction notes

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