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 1040776ノート

反応式

HRID 1040776 の反応式
[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

参加物

4

反応物 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

生成物 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-benzenesulfonamide収率 70.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a5bf76935c4441d5bb5301817a0941a9
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

反応ノート

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