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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
Notes
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Reaction equation

HRID 75969 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

HCID 50914585
3-(4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxopyrrolidin-3-yloxy)-N-(4-methylthiazol-2-yl)benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c3472dd1329b4842b0869dd491a8adc9
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835469B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes