2-(5-Methyl-1,3,4-oxadiazol-2-yl)benzoic acid → 2-(5-Methyl-1,3,4-oxadiazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

HRID 1750611Notes

Reaction equation

HRID 1750611 reaction equation
CO[C:3]1[CH:27]=[CH:26][C:25](C)=[CH:24][C:4]=1[C:5]([NH:7][C@H:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[NH:13][C:14]1[CH:19]=[N:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1)=[O:6].Cl.FC(F)(F)C1N=CC(N[C@H]2CCC[C@@H]2N)=NC=1.[CH3:47][C:48]1[O:52][C:51](C2C=CC=CC=2C(O)=O)=[N:50][N:49]=1>>[CH3:47][C:48]1[O:52][C:51]([C:3]2[CH:27]=[CH:26][CH:25]=[CH:24][C:4]=2[C:5]([NH:7][C@H:8]2[CH2:12][CH2:11][CH2:10][C@@H:9]2[NH:13][C:14]2[CH:19]=[N:18][C:17]([C:20]([F:21])([F:23])[F:22])=[CH:16][N:15]=2)=[O:6])=[N:50][N:49]=1

Participants

4

Reactant 3

HCID 337001972-(5-Methyl-1,3,4-oxadiazol-2-yl)benzoic acidHCID 118308118(1S,2S)-1-N-[5-(Trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 1183082742-Methoxy-5-methyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Product 1

HCID 1183081892-(5-Methyl-1,3,4-oxadiazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Procedure

Prepared according to the procedure for 2-methoxy-5-methyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide (Example 37) from (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14; 75 mg, 0.27 mmol) and 2-(5-methyl-1,3,4-oxadiazol-2-yl)benzoic acid (CAS number 898289-64-0; 75 mg, 0.37 mmol) except this was purified by column chromatography (silica, 40-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was purified by column chromatography (silica, 40-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-a338ceabaf8e4d859ab0849c866083be
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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