2-Chloro-5-(trifluoromethyl)pyrimidine → 2-(2H-1,2,3-Triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrimidin-2-yl]amino}cyclopentyl]benzamide

HRID 1750588Notes

Reaction equation

HRID 1750588 reaction equation
COC1C=CC=C(OC)C=1C(N[C@H]1CCC[C@@H]1[NH:13][C:14]1C=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1)=O.Cl.[NH2:31][C@H:32]1[CH2:36][CH2:35][CH2:34][C@@H:33]1[NH:37][C:38](=[O:50])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[N:45]1[N:49]=[CH:48][CH:47]=[N:46]1.ClC1N=CC(C(F)(F)F)=CN=1>>[N:49]1[N:45]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[C:38]([NH:37][C@H:33]2[CH2:34][CH2:35][CH2:36][C@@H:32]2[NH:31][C:14]2[N:13]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=2)=[O:50])[N:46]=[CH:47][CH:48]=1

Participants

4

Reactant 3

HCID 133170192-Chloro-5-(trifluoromethyl)pyrimidineHCID 118025476N-[(1S,2S)-2-Aminocyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride2×HCID 1183082042,6-Dimethoxy-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide

Product 1

HCID 1183081832-(2H-1,2,3-Triazol-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrimidin-2-yl]amino}cyclopentyl]benzamide

Procedure

Prepared according to the procedure for 2,6-dimethoxy-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]benzamide (Example 1) from N-[(1S,2S)-2-amino cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 4; 100 mg, 0.325 mmol) and 2-chloro-5-(trifluoromethyl)pyrimidine (CAS number 69034-12-4; 59.3 mg, 0.325 mmol). The crude reaction was filtered through cotton wool before being purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.

Workup

  1. customPrepared
  2. customThe crude reaction
  3. filtrationwas filtered through cotton wool
  4. custombefore being purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia)

Sources & evidence

ORD record
ord-9dab0a9bc64142ce9dab7ffc5af26b7b
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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