2-Amino-4-methylthiazole → 3-(4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxopyrrolidin-3-yloxy)-N-(4-methylthiazol-2-yl)benzamide

HRID 75969

반응식

HRID 75969 반응식
Cl.CN(C)CCCN=C=NCC.COCC(OC1C=C(C=C(OC2C=CC(C3OC(C)=NN=3)=CC=2)C=1)C(O)=O)C.[CH3:41][C:42]1[O:46][C:45]([C:47]2[CH:70]=[CH:69][C:50]([O:51][C:52]3[CH:53]=[C:54]([CH:58]=[C:59]([O:61][CH:62]4[CH2:66][CH2:65][N:64]([CH3:67])[C:63]4=[O:68])[CH:60]=3)[C:55](O)=[O:56])=[CH:49][CH:48]=2)=[N:44][N:43]=1.[NH2:71][C:72]1[S:73][CH:74]=[C:75]([CH3:77])[N:76]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:41][C:42]1[O:46][C:45]([C:47]2[CH:48]=[CH:49][C:50]([O:51][C:52]3[CH:53]=[C:54]([CH:58]=[C:59]([O:61][CH:62]4[CH2:66][CH2:65][N:64]([CH3:67])[C:63]4=[O:68])[CH:60]=3)[C:55]([NH:71][C:72]3[S:73][CH:74]=[C:75]([CH3:77])[N:76]=3)=[O:56])=[CH:69][CH:70]=2)=[N:44][N:43]=1

참가 물질

7

반응물 4

HCID 741432-Amino-4-methylthiazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 669719313-(1-Methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acidHCID 669722263-(4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxo pyrrolidin-3-yloxy)benzoic acid

생성물 1

HCID 509145853-(4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxopyrrolidin-3-yloxy)-N-(4-methylthiazol-2-yl)benzamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

4-(Dimethylamino)pyridine (DMAP) (0.149 g), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI.HCl) (0.524 g) were added to a solution of 3-(1-Methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acid (0.5 g) (Intermediate 1) in dry DCM under nitrogen at 0-5° C. 2-amino-4-methyl thiazole (0.134 g) was added and the mixture was stirred for 16 h at room temperature. It was diluted with commercially available DCM. Organic phase was washed with dil HCl, saturated solution of NaHCO3, water, brine, dried over Na2SO4, filtered and concentrated in vacuo to get the crude residue. The residue was chromatographed to yield pure titled compound (0.3 g) as a white solid.

후처리

  1. washOrganic phase was washed with dil HCl, saturated solution of NaHCO3, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto get the crude residue
  6. customThe residue was chromatographed

출처 및 근거

ORD 기록
ord-c3472dd1329b4842b0869dd491a8adc9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835469B2

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