2-Ethoxy-5-methylbenzoic acid → 2-Ethoxy-5-methyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

HRID 1750596Notes

Reaction equation

HRID 1750596 reaction equation
BrC1C(C(N[C@H]2CCC[C@@H]2NC2C=NC(C(F)(F)F)=CN=2)=O)=NC=CC=1.Cl.[F:28][C:29]([F:44])([F:43])[C:30]1[N:31]=[CH:32][C:33]([NH:36][C@H:37]2[CH2:41][CH2:40][CH2:39][C@@H:38]2[NH2:42])=[N:34][CH:35]=1.[CH2:45]([O:47][C:48]1[CH:56]=[CH:55][C:54]([CH3:57])=[CH:53][C:49]=1[C:50](O)=[O:51])[CH3:46]>>[CH2:45]([O:47][C:48]1[CH:56]=[CH:55][C:54]([CH3:57])=[CH:53][C:49]=1[C:50]([NH:42][C@H:38]1[CH2:39][CH2:40][CH2:41][C@@H:37]1[NH:36][C:33]1[CH:32]=[N:31][C:30]([C:29]([F:28])([F:43])[F:44])=[CH:35][N:34]=1)=[O:51])[CH3:46]

Participants

4

Reactant 3

HCID 189546022-Ethoxy-5-methylbenzoic acidHCID 118308118(1S,2S)-1-N-[5-(Trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 1183082783-Bromo-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide

Product 1

HCID 1183080612-Ethoxy-5-methyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Procedure

Prepared according to the procedure for 3-bromo-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide (Example 28) from (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14, 75 mg, 0.27 mmol) and 2-ethoxy-5-methylbenzoic acid (CAS number 854645-34-4; 57 mg, 0.32 mmol) and was then purified by column chromatography (silica, 40-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customPrepared
  2. customwas then purified by column chromatography (silica, 40-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-306ed340bebb469bbaea27b164f995a6
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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