Diisopropylethylamine → Methyl 5-{[4-methyl-5-(5-{[(2-morpholin-4-ylethyl)amino]sulfonyl}-2-thienyl)-1,3-thiazol-2-yl]amino}-5-oxopentanoate

HRID 1360861

반응식

HRID 1360861 반응식
[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

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69931945-Methoxy-5-oxopentanoateHCID 119983065-(2-amino-4-methyl-1,3-thiazol-5-yl)-N-(2-morpholin-4-ylethyl)thiophene-2-sulfonamide

생성물 1

HCID 11998428Methyl 5-{[4-methyl-5-(5-{[(2-morpholin-4-ylethyl)amino]sulfonyl}-2-thienyl)-1,3-thiazol-2-yl]amino}-5-oxopentanoate수율 61.18%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-65b23ed3f76e4cc0b7e2f1ab2d73a8ff
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879888B2

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