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Glycolic Acid → N-Cyclopropyl-4'-{5-[(glycoloylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31484
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HRID 31484 반응식
[NH2:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]([NH:23][CH:24]4[CH2:26][CH2:25]4)=[O:22])[CH:15]=3)=[CH:10][CH:9]=2)=[N:5][N:4]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:46](O)(=[O:49])[CH2:47][OH:48]>C(Cl)Cl.CO.C(Cl)CCl>[CH:24]1([NH:23][C:21]([C:16]2[CH:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([C:6]4[O:7][C:3]([CH2:2][NH:1][C:47](=[O:48])[CH2:46][OH:49])=[N:4][N:5]=4)=[CH:13][CH:12]=3)[C:19]([CH3:20])=[CH:18][CH:17]=2)=[O:22])[CH2:26][CH2:25]1
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참가 물질

8

반응물 4

HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 99978914'-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

생성물 1

HCID 11742059N-Cyclopropyl-4'-{5-[(glycoloylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매
HCID 887Methanol용매
HCID 6344Dichloromethane용매

실험 절차

4′-[5-(Aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Example 53) (30 mg), HOBt (11.7 mg), EDC (19.8 mg), DIPEA (0.018 ml) and glycolic acid (6.6 mg) were mixed in DCM (6 ml) and methanol (1 ml) and the reactions stirred at room temperature for 96 hours. The reaction was reduced to dryness under vacuum and the residue partitioned between DCM and water. The organic phase was evaporated and the residue purified by bond-elut (silica, 5 g) eluting with an ethyl acetate/cyclohexane gradient and then by preparative HPLC to give, after evaporation of the solvents, N-cyclopropyl-4′-{5-[(glycoloylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide.

후처리

  1. customthe residue partitioned between DCM and water
  2. customThe organic phase was evaporated
  3. customthe residue purified by bond-elut (silica, 5 g)
  4. washeluting with an ethyl acetate/cyclohexane gradient
  5. customby preparative HPLC to give
  6. customafter evaporation of the solvents, N-cyclopropyl-4′-{5-[(glycoloylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide

출처 및 근거

ORD 기록
ord-185c1fae696745f7b51017f6b1de24bf
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07425555B2

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