3-[1,2,3]Triazol-2-yl-pyridine-2-carboxylic acid → N-[(1S,2S)-2-{[3-Ethyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

HRID 1750688Notes

Reaction equation

HRID 1750688 reaction equation
ClC1C(N[C@H]2CCC[C@@H]2N[C:19]([C:21]2[C:26]([N:27]3[N:31]=[CH:30][CH:29]=[N:28]3)=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:20])=NC=C(C(F)(F)F)C=1.Cl.[CH2:33]([C:35]1[C:36]([NH:45][C@H:46]2[CH2:50][CH2:49][CH2:48][C@@H:47]2[NH2:51])=[N:37][CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[N:40]=1)[CH3:34].N1N(C2C(C(O)=O)=NC=CC=2)N=CC=1>>[CH2:33]([C:35]1[C:36]([NH:45][C@H:46]2[CH2:50][CH2:49][CH2:48][C@@H:47]2[NH:51][C:19]([C:21]2[C:26]([N:27]3[N:31]=[CH:30][CH:29]=[N:28]3)=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:20])=[N:37][CH:38]=[C:39]([C:41]([F:44])([F:42])[F:43])[N:40]=1)[CH3:34]

Participants

4

Reactant 3

HCID 667422883-[1,2,3]Triazol-2-yl-pyridine-2-carboxylic acidHCID 118308132(1S,2S)-1-N-[3-Ethyl-5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 118308168N-[(1S,2S)-2-{[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

Product 1

HCID 118308154N-[(1S,2S)-2-{[3-Ethyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-{ [3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide (Example 122) from (1S,2S)-1-N-[3-ethyl-5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 41; 266 mg, 0.86 mmol) and 3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxylic acid (CAS number 1252907-86-0; 179 mg, 0.94 mmol) except this was further purified by reverse phase chromatography (C18 silica, 5-100% water (with 0.05% ammonia)/acetonitrile) to afford the title compound.

Workup

  1. customPrepared
  2. customfurther purified by reverse phase chromatography (C18 silica, 5-100% water (with 0.05% ammonia)/acetonitrile)

Sources & evidence

ORD record
ord-cbc4606653f54118b8fd903fee85175f
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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