Water → 6-[2,3-Dihydro-2-oxo-1H-benzimidazol-1-ylmethyl]-1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylic acid, methyl ester

HRID 131576노트

반응식

HRID 131576 반응식
Cl[C:2]1[N:3]=[C:4](C)[N:5]([CH2:8][C:9]2[S:24][C:12]3[N:13]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:14](=[O:19])[N:15]([CH3:18])[C:16](=[O:17])[C:11]=3[C:10]=2[C:25](N2C[C@H](O)CO2)=[O:26])[C:6]=1Cl.ClC1N[C:37]2C=C[CH:41]=[CH:40][C:38]=2N=1.[C:44](=O)([O-])[O-:45].[K+].[K+].CN(C=O)C.[OH2:55]>C(OCC)(=O)C>[O:55]=[C:4]1[N:5]([CH2:8][C:9]2[S:24][C:12]3[N:13]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:14](=[O:19])[N:15]([CH3:18])[C:16](=[O:17])[C:11]=3[C:10]=2[C:25]([O:45][CH3:44])=[O:26])[C:6]2[CH:37]=[CH:38][CH:40]=[CH:41][C:2]=2[NH:3]1

참가 물질

7

반응물 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 785722-ChlorobenzimidazoleHCID 101425596-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-5-[4-(S)-hydroxy-2-isoxazolidinylcarbonyl]-3-methyl-1-(isobutyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

생성물 1

HCID 866227116-[2,3-Dihydro-2-oxo-1H-benzimidazol-1-ylmethyl]-1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylic acid, methyl ester

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

The product of example 3 part b) (0.5 g, 1.28 mmol), 2-chlorobenzimidazole (0.21 g, 1.37 mmol), potassium carbonate (0.36 g, 2.6 mmol) and DMF (10 ml) were stirred for 1.5 h. Ethyl acetate and water were added to the reaction mixture. The two phases were separated, the organic layer was dried (MgSO4) and then concentrated in vacuo. The residue was purified by biotage eluting with dichloromethane to give the sub-title compund as a pale yellow solid, 0.36 g (61%). δ 1HD6DMSO 0.83 and 0.91 (6H, d), 2.1-2.22 (1H,m), 3.38 (3H,s), 3.67 (2H,d), 4.1 (3H,s), 5.58 (2H,s), 7.26-7.38 (2H,m), 7.41-7.48 (1H,m) and 7.7-7.8 (1H,m).

후처리

  1. customThe two phases were separated
  2. dry with materialthe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by biotage
  5. washeluting with dichloromethane
  6. customto give the sub-title compund as a pale yellow solid, 0.36 g (61%)

출처 및 근거

ORD 기록
ord-56eb70ac79244e5a9cba5c5fb95804f0
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384950B2

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