3,5-difluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid → HCID 118308338, compound

HRID 1750665Notes

Reaction equation

HRID 1750665 reaction equation
ClC1C=CC(N2N=CC=N2)=C(C=1)C(N[C@H]1CCC[C@@H]1NC1C=CC(C(F)(F)F)=CN=1)=O.Cl.[F:33][C:34]([F:49])([F:48])[C:35]1[CH:36]=[CH:37][C:38]([NH:41][C@H:42]2[CH2:46][CH2:45][CH2:44][C@@H:43]2[NH2:47])=[N:39][CH:40]=1.[F:50][C:51]1[C:52]([N:61]2[N:65]=[CH:64][CH:63]=[N:62]2)=[C:53]([CH:57]=[C:58]([F:60])[CH:59]=1)[C:54](O)=[O:55]>>[F:50][C:51]1[C:52]([N:61]2[N:65]=[CH:64][CH:63]=[N:62]2)=[C:53]([CH:57]=[C:58]([F:60])[CH:59]=1)[C:54]([NH:47][C@H:43]1[CH2:44][CH2:45][CH2:46][C@@H:42]1[NH:41][C:38]1[CH:37]=[CH:36][C:35]([C:34]([F:33])([F:48])[F:49])=[CH:40][N:39]=1)=[O:55]

Participants

4

Reactant 3

HCID 1177279223,5-difluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid2×HCID 1183080695-Chloro-2-(2H-1,2,3-triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamideHCID 118308256(1S,2S)-1-N-[5-(Trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride2×

Product 1

HCID 118308338HCID 118308338, compound

Procedure

Prepared according to the procedure for 5-chloro-2-(2H-1,2,3-triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide (Example 97) from (1S,2S)-1-N-[5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 1; 50 mg, 0.20 mmol) and 3,5-difluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 40a; 46 mg, 0.20 mmol) except this was purified by column chromatography (silica, 0-30% ethyl acetate/n-hexane) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was purified by column chromatography (silica, 0-30% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-427b646f1a784753840c24b1c133f452
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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