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

HRID 1750698Notes

Reaction equation

HRID 1750698 reaction equation
C(OC1C=NC(C2C=CC=CC=2C(N[C@H]2CCC[C@@H]2NC2C=NC(C(F)(F)F)=CN=2)=O)=NC=1)C.Cl.[F:36][C:37]1[C:38]([NH:47][C@H:48]2[CH2:52][CH2:51][CH2:50][C@@H:49]2[NH2:53])=[N:39][CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1.[F:54][C:55]1[CH:56]=[CH:57][C:58]([C:64]2[N:69]=[CH:68][CH:67]=[CH:66][N:65]=2)=[C:59]([CH:63]=1)[C:60](O)=[O:61]>>[F:54][C:55]1[CH:56]=[CH:57][C:58]([C:64]2[N:65]=[CH:66][CH:67]=[CH:68][N:69]=2)=[C:59]([CH:63]=1)[C:60]([NH:53][C@H:49]1[CH2:50][CH2:51][CH2:52][C@@H:48]1[NH:47][C:38]1[C:37]([F:36])=[CH:42][C:41]([C:43]([F:46])([F:44])[F:45])=[CH:40][N:39]=1)=[O:61]

Participants

4

Reactant 3

HCID 670869505-Fluoro-2-(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 1183081285-Fluoro-N-[(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: 200 mg, 0.76 mmol) and 5-fluoro-2-(pyrimidin-2-yl)benzoic acid (CAS number 1293284-57-7; 166 mg, 0.76 mmol) except after the reaction was complete it was concentrated in vacuo and the residue was purified by reverse phase column chromatography (C18 silica, 0-100% water (0.05% ammonia)/methanol), then by column chromatography (silica, 0-50% ethyl acetate/petrol) and then triturated with DCM/petrol to afford the title compound.

Workup

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

Sources & evidence

ORD record
ord-46b98cf6e6b84354a8e7f1722a6ed81b
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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