Cyclopentylamine → HCID 44234766, compound

HRID 1093791Notes

Reaction equation

HRID 1093791 reaction equation
CCN(C(C)C)C(C)C.[CH:10]1([N:15]2[CH:19]=[C:18]([C:20]([OH:22])=O)[N:17]=[N:16]2)[CH2:14][CH2:13][CH2:12][CH2:11]1.C1(N)CCCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:51][CH2:52][C:53]([N:55]1[CH2:60][CH2:59][CH:58]([O:61][C:62]2[CH:63]=[N:64][CH:65]=[C:66]([Cl:68])[CH:67]=2)[CH2:57][CH2:56]1)=[O:54]>CN(C=O)C.O>[Cl:68][C:66]1[CH:67]=[C:62]([O:61][CH:58]2[CH2:57][CH2:56][N:55]([C:53](=[O:54])[CH2:52][NH:51][C:20]([C:18]3[N:17]=[N:16][N:15]([CH:10]4[CH2:11][CH2:12][CH2:13][CH2:14]4)[CH:19]=3)=[O:22])[CH2:60][CH2:59]2)[CH:63]=[N:64][CH:65]=1

Participants

9

Reactant 6

HCID 2906CyclopentylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 62061226HCID 62061226, compoundHCID 665916722-Amino-1-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-ethanone hydrochloride

Product 1

HCID 44234766HCID 44234766, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (300 mg, 2.3 mmol) was added to a stirred solution of 1-Cyclopentyl-1H-[1,2,3]triazole-4-carboxylic acid (75 mg, 0.41 mmol (prepared by the method used for the synthesis of Intermediate 64, starting from cyclopentylamine) in DMF (5 mL) followed by HOBt (61 mg, 0.4 mmol) and EDCI (200 mg, 1 mmol). After 2 minutes of stirring, 2-amino-1-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (156 mg, 0.5 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. Cold water was then added and filtered the precipitate was filtered. The solid obtained was purified by recrystallisation from a solvent system EtOAc:hexane:MeOH (3:7:0.2) to afford 98 mg (55% Yield) of 1-cyclopentyl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+ 433, 98.59%. 1H NMR (300 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.34 (m, 2H), 8.24 (s, 1H), 7.74 (s, 1H), 5.1 (m, 1H), 4.9 (m, 1H), 4.2 (d, 2H), 4.0 (bs, 1H), 3.8 (bs, 1H), 3.4 (s, 1H), 3.3 (m, 1H), 2.3 (m, 2H), 2.1 (m, 4H), 1.9-1.5 (m, 6H).

Workup

  1. customprepared by the method
  2. additionwas added
  3. stirringthe resulting mixture was stirred at ambient temperature overnight
  4. filtrationfiltered the precipitate
  5. filtrationwas filtered
  6. customThe solid obtained
  7. customwas purified by recrystallisation from a solvent system EtOAc:hexane:MeOH (3:7:0.2)

Sources & evidence

ORD record
ord-4fc2633cb1e048f592698b6960128ec6
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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