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

HRID 1750700Notes

Reaction equation

HRID 1750700 reaction equation
C(OC1C=NC([C:10]2[CH:34]=[CH:33][CH:32]=[CH:31][C:11]=2[C:12]([NH:14][C@H:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[NH:20][C:21]2[CH:26]=[N:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=2)=[O:13])=NC=1)C.Cl.[CH3:36]N(C1C=NC(C(F)(F)F)=CN=1)[C@H]1CCC[C@@H]1N.[CH3:54][C:55]1[N:59]=[C:58](C2C=CC=CC=2C(O)=O)[O:57][N:56]=1>>[CH3:54][C:55]1[N:59]=[C:58]([C:10]2[CH:34]=[CH:33][CH:32]=[CH:31][C:11]=2[C:12]([NH:14][C@H:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[NH:20][C:21]2[C:26]([CH3:36])=[N:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][N:22]=2)=[O:13])[O:57][N:56]=1

Participants

4

Reactant 3

HCID 231463052-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acidHCID 118308127(1S,2S)-1-N-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 1183081672-(5-Ethoxypyrimidin-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Product 1

HCID 1183083422-(3-Methyl-1,2,4-oxadiazol-5-yl)-N-[(1S,2S)-2-{[3-methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Procedure

Prepared according to the procedure for 2-(5-Ethoxypyrimidin-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide (Example 135) from (1S,2S)-1-N-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 23; 452 mg, 1.74 mmol) and 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid (CAS number 475105-77-2; 355 mg, 1.74 mmol) except after the reaction was complete it was partitioned between DCM and a saturated solution of sodium bicarbonate, filtered through a hydrophobic frit. The organics were loaded directly on to a cation/anion mixed mode cartridge, eluted with DCM and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-100% ethyl acetate/petrol) and then recrystallised from MTBE/heptane to afford the title compound.

Workup

  1. customPrepared
  2. customwas partitioned between DCM
  3. filtrationa saturated solution of sodium bicarbonate, filtered through a hydrophobic frit
  4. additionmixed mode cartridge
  5. washeluted with DCM
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (silica, 0-100% ethyl acetate/petrol)
  8. customrecrystallised from MTBE/heptane

Sources & evidence

ORD record
ord-e68bcef4cac6486fbd9cc393217adb42
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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