Potassium Carbonate → HCID 67356097, compound

HRID 1850545Notes

Reaction equation

HRID 1850545 reaction equation
[CH3:1][N:2]([CH3:36])[C:3]([C:5]1[N:30]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([N:22]4[CH2:28][CH:27]5[CH2:29][CH:24]([CH2:25][NH:26]5)[CH2:23]4)=[O:21])=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].CCN(C(C)C)C(C)C.C(=O)([O-])[O-].[K+].[K+].[F:52][C:53]([F:64])([F:63])[CH2:54]OS(C(F)(F)F)(=O)=O>O1CCOCC1.C(Cl)Cl>[CH3:1][N:2]([CH3:36])[C:3]([C:5]1[N:30]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([N:22]4[CH2:28][CH:27]5[CH2:29][CH:24]([CH2:25][N:26]5[CH2:54][C:53]([F:64])([F:63])[F:52])[CH2:23]4)=[O:21])=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 81531DiisopropylethylamineHCID 53377947HCID 53377947, compound

Product 1

HCID 67356097HCID 67356097, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

In a 100 ml round bottom flask was combined 7-Cyclopentyl-2-[5-(3,6-diaza-bicyclo[3.2.1]octane-3-carbonyl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (165 mg, 0.294 mmol) and DIPEA (0.128 ml, 0.735 mmol) which were diluted in Dioxane (6.00 ml) gave a yellowish heterogeneous solution. To this mixture was then added potassium carbonate (406 mg, 2.94 mmol) and trifluoroethyltriflate (0.106 ml, 0.735 mmol). The reaction was heated to 50° C. for 18 h. LCMS showed 100% conversion. The mixture was diluted in DCM, and washed with sat'd aq solution of NaHCO3, followed by a brine wash. The organic layer was then separated, dried over MgSO4 and evaporated to give a yellowish solid. This solid was triturated with EtOAc to give 98 mg of 7-Cyclopentyl-2-{5-[6-(2,2,2-trifluoro-ethyl)-3,6-diaza-bicyclo[3.2.1]octane-3-carbonyl]-pyridin-2-ylamino}-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide in 58% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.95 (1H, s), 8.84 (1H, s), 8.30-8.40 (2H, m), 7.81-7.83 (1H, d), 6.65 (1H, s), 4.71-4.78 (1H, quin.), 3.23-3.42 (7H, m), 3.06 (7H, br. s.), 2.30-2.45 (2H, br. s.), 1.99 (4H, br. s.), 1.55-1.75 (4H, d), 1.24-1.35 (2H, br. s). MS (ESI) m/e (M+H+): 570.9

Workup

  1. customIn a 100 ml round bottom flask was combined
  2. customgave a yellowish heterogeneous solution
  3. washwashed with sat'd aq solution of NaHCO3
  4. washwash
  5. customThe organic layer was then separated
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give a yellowish solid
  9. customThis solid was triturated with EtOAc

Sources & evidence

ORD record
ord-93e9b2be773f458fa25e01aa88c78c33
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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