Diisopropylethylamine → HCID 11998428、化合物

HRID 1360861

反応式

HRID 1360861 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:8]2[S:12][C:11]([S:13]([NH:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)(=[O:15])=[O:14])=[CH:10][CH:9]=2)=[C:5]([CH3:7])[N:6]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:47]([O:55][CH3:56])(=[O:54])[CH2:48][CH2:49][CH2:50][C:51]([O-])=[O:52].C(N(CC)C(C)C)(C)C>C1COCC1>[CH3:7][C:5]1[N:6]=[C:2]([NH:1][C:51](=[O:52])[CH2:50][CH2:49][CH2:48][C:47]([O:55][CH3:56])=[O:54])[S:3][C:4]=1[C:8]1[S:12][C:11]([S:13]([NH:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)(=[O:15])=[O:14])=[CH:10][CH:9]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69931945-Methoxy-5-oxopentanoateHCID 11998306HCID 11998306、化合物

生成物 1

HCID 11998428HCID 11998428、化合物収率 61.18%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a degassed solution of 5-(2-amino-4-methyl-1,3-thiazol-5-yl)-N-(2-morpholin-4-ylethyl)thiophene-2-sulfonamide (6) (100 mg; 0.22 mmol; 1 eq) in anhydrous THF (10 ml), N-[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate (104.4 mg; 0.33 mmol; 1.50 eq), mono-methyl glutarate (68 μl; 0.54 mmol; 2.50 eq) and N,N-diisopropylethylamine (148 μl; 0.87 mmol; 4 eq) are added successively. The reaction mixture is stirred at room temperature for three days. Solvents are evaporated under vacuum. The resulting crude product is dissolved in EtOAc and washed with NH4Cl sat. solution, water, brine and dried over MgSO4. After evaporation of the solvents, the crude product is purified by flash chromatography (CH3C1/MeOH gradient from 1/0 to 1/1 over 40 min), affording Compound (7) as a yellow solid (68.5 mg; 61.18%).

後処理

  1. customSolvents are evaporated under vacuum
  2. dissolutionThe resulting crude product is dissolved in EtOAc
  3. washwashed with NH4Cl sat. solution, water, brine
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvents
  6. customthe crude product is purified by flash chromatography (CH3C1/MeOH gradient from 1/0 to 1/1 over 40 min)

出典と根拠

ORDレコード
ord-65b23ed3f76e4cc0b7e2f1ab2d73a8ff
出典データセット
uspto-grants-2011_02
特許番号
US07879888B2

関連ノート

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