Potassium Carbonate → 2-[2-(10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-4-ylamino)-5-chloro-pyrimidin-4-ylamino]-N-methyl-benzenesulfonamide

HRID 1040776Notes

Reaction equation

HRID 1040776 reaction equation
[Cl:1][C:2]1[C:3]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:35]([NH:38][CH3:39])(=[O:37])=[O:36])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]3[C:17](=[CH:18][CH:19]=2)[CH:16]2[CH2:20][CH2:21][CH:12]3[CH2:13][N:14](C(=O)C(F)(F)F)[CH2:15]2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:12]12[CH2:21][CH2:20][CH:16]([CH2:15][NH:14][CH2:13]1)[C:17]1[C:11]2=[CH:10][C:9]([NH:8][C:5]2[N:4]=[C:3]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35]([NH:38][CH3:39])(=[O:37])=[O:36])[C:2]([Cl:1])=[CH:7][N:6]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 873302302-{5-Chloro-2-(10-(2,2,2-trifluoro-acetyl)-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-4-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzenesulfonamide

Product 1

HCID 668296232-[2-(10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-4-ylamino)-5-chloro-pyrimidin-4-ylamino]-N-methyl-benzenesulfonamideYield 70.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{5-Chloro-2-[10-(2,2,2-trifluoro-acetyl)-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-4-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzenesulfonamide (510 mg, 0.878 mmol) was dissolved in methanol (20 mL) and potassium carbonate (727 mg, 5.27 mmol, 6.0 eq) was added. The reaction was stirred at room temperature for 72 hours and then concentrated under reduced pressure. The residue was taken up in water (30 mL) and the product was extracted into EtOAc (3×30 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by basic alumina chromatography using a gradient of 0-5% MeOH/CH2Cl2 as the eluting solvent to obtain 2-[2-(10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-4-ylamino)-5-chloro-pyrimidin-4-ylamino]-N-methyl-benzenesulfonamide as a white foam (300 mg, 70%). LCMS (m/e) 485 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 9.11 (bs, 1H), 8.49 (dd, 1H, J=1.0 and 8.4 Hz), 8.12 (s, 1H), 7.96 (dd, 1H, J=1.6 and 8.0 Hz), 7.60-7.52 (m, 1H), 7.33-7.19 (m, 3H), 7.00 (d, 1H, J=7.7 Hz), 6.95 (bs, 1H), 2.99-2.90 (m, 3H), 2.87-2.76 (m, 3H), 2.64 (s, 3H), 2.08-2.00 (m, 2H), 1.84-1.77 (m, 2H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionthe product was extracted into EtOAc (3×30 mL)
  3. dry with materialThe combined organic layers were dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by basic alumina chromatography

Sources & evidence

ORD record
ord-a5bf76935c4441d5bb5301817a0941a9
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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