2-(Pyrimidin-2-yl)benzoic acid → N-[(1S,2S)-2-{[3-Fluoro-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]-2-(pyrimidin-2-yl)benzamide

HRID 1750697Notes

Reaction equation

HRID 1750697 reaction equation
C(O[C:4]1[CH:5]=[N:6][C:7]([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]2C=N[C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=2)=[O:13])=[N:8][CH:9]=1)C.Cl.[F:36][C:37]1C(N[C@H]2CCC[C@@H]2N)=NC=C(C(F)(F)F)[CH:42]=1.N1C=CC=NC=1C1C=CC=CC=1C(O)=O>>[F:36][C:37]1[C:21]([NH:20][C@H:16]2[CH2:17][CH2:18][CH2:19][C@@H:15]2[NH:14][C:12](=[O:13])[C:11]2[CH:31]=[CH:32][CH:33]=[CH:34][C:10]=2[C:7]2[N:6]=[CH:5][CH:4]=[CH:9][N:8]=2)=[N:22][CH:23]=[C:24]([C:27]([F:28])([F:30])[F:29])[CH:42]=1

Participants

4

Reactant 3

HCID 198021182-(Pyrimidin-2-yl)benzoic acidHCID 1183081672-(5-Ethoxypyrimidin-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamideHCID 118308208(1S,2S)-1-N-[3-Fluoro-5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride2×

Product 1

HCID 118308255N-[(1S,2S)-2-{[3-Fluoro-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]-2-(pyrimidin-2-yl)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-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 34: 263 mg, 1.00 mmol) and 2-(pyrimidin-2-yl)benzoic acid (CAS number 400892-62-8; 200 mg, 1.00 mmol) except after the reaction was complete it was concentrated in vacuo and the residue was purified by column chromatography (silica, 0-50% ethyl acetate/petrol) and then was purified by reverse phase column chromatography (C18 silica, 0-100% water (0.05% ammonia)/methanol) and triturated with DCM/petrol. The product was further purified by reverse phase column chromatography (C18 silica, 0-100% water (0.1% ammonia)/acetonitrile to afford the title compound.

Workup

  1. customPrepared
  2. concentrationwas concentrated in vacuo
  3. customthe residue was purified by column chromatography (silica, 0-50% ethyl acetate/petrol)
  4. customwas purified by reverse phase column chromatography (C18 silica, 0-100% water (0.05% ammonia)/methanol) and
  5. customtriturated with DCM/petrol
  6. customThe product was further purified by reverse phase column chromatography (C18 silica, 0-100% water (0.1% ammonia)/acetonitrile

Sources & evidence

ORD record
ord-990e16f4090e47768c4e54f2317c6dd4
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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