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

HRID 1750704Notes

Reaction equation

HRID 1750704 reaction equation
C[C@]1(NC2C=NC(C(F)(F)F)=CN=2)CCC[C@@H]1NC(C1C(C2N=CC=CN=2)=CC=CN=1)=O.[CH3:33][C@:34]1([NH:40][C:41]2[CH:46]=[N:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][N:42]=2)[CH2:38][CH2:37][CH2:36][C@@H:35]1[NH2:39].[CH3:51][C:52]1[N:56]=[C:55]([C:57]2[CH:65]=[CH:64][CH:63]=[CH:62][C:58]=2[C:59](O)=[O:60])[O:54][N:53]=1>>[CH3:51][C:52]1[N:56]=[C:55]([C:57]2[CH:65]=[CH:64][CH:63]=[CH:62][C:58]=2[C:59]([NH:39][C@H:35]2[CH2:36][CH2:37][CH2:38][C@:34]2([CH3:33])[NH:40][C:41]2[CH:46]=[N:45][C:44]([C:47]([F:50])([F:48])[F:49])=[CH:43][N:42]=2)=[O:60])[O:54][N:53]=1

Participants

4

Reactant 3

HCID 231463052-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acidHCID 118308048(1S,2S)-1-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine2×HCID 118308050N-[(1S,2S)-2-Methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(pyrimidin-2-yl)pyridine-2-carboxamide

Product 1

HCID 1183083062-(3-Methyl-1,2,4-oxadiazol-5-yl)-N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(pyrimidin-2-yl)pyridine-2-carboxamide (Example 144) from (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 190 mg, 0.73 mmol) and 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid (CAS number 475105-77-2; 179 mg, 0.88 mmol). After work-up, the crude material was loaded directly on to a cation/anion mixed mode cartridge, eluted with DCM and concentrated in vacuo. This was then recrystallised from MTBE to afford the title compound.

Workup

  1. customPrepared
  2. additionmixed mode cartridge
  3. washeluted with DCM
  4. concentrationconcentrated in vacuo
  5. customThis was then recrystallised from MTBE

Sources & evidence

ORD record
ord-d71218aa8e1e4d3b9d1e5769e2a22a0d
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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