Cyclopentylamine → HCID 59362941, compound

HRID 1668831Notes

Reaction equation

HRID 1668831 reaction equation
Cl.CN(C)CCCN=C=NCC.[N:13]1([C:19]2[N:24]=[C:23]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]4([C:36](O)=[O:37])[CH2:35][CH2:34][CH2:33]4)=[CH:28][CH:27]=3)[C:22]3[CH2:39][CH2:40][CH2:41][C:21]=3[N:20]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(C(C)C)CC)(C)C.[CH:51]1([NH2:56])[CH2:55][CH2:54][CH2:53][CH2:52]1>CN(C)C=O>[CH:51]1([NH:56][C:36]([C:32]2([C:29]3[CH:28]=[CH:27][C:26]([NH:25][C:23]4[C:22]5[CH2:39][CH2:40][CH2:41][C:21]=5[N:20]=[C:19]([N:13]5[CH2:14][CH2:15][O:16][CH2:17][CH2:18]5)[N:24]=4)=[CH:31][CH:30]=3)[CH2:33][CH2:34][CH2:35]2)=[O:37])[CH2:55][CH2:54][CH2:53][CH2:52]1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59362928HCID 59362928, compound

Product 1

HCID 59362941HCID 59362941, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.48 g, 2.5 mmol) was added to a mixture of 1-[4-(2-morpholin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid (0.5 g, 1.2 mmol), 1-hydroxybenzotrialzole (0.09 g, 0.65 mmol), diisopropylethylamine (0.43 mL, 2.5 mmol), and cyclopentylamine (0.13 mL, 1.3 mmol) in anhydrous dimethylformamide and stirred at a temperature in the range of 15° C. to 25° C. under N2 for 16 hours. The reaction was quenched by addition of water. The precipitated solid was filtered, washed with water and dried in vacuo. The crude was purified by column chromatography (silica gel) to afford the title compound as a white solid (0.26 g, 45% yield).

Workup

  1. customThe reaction was quenched by addition of water
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water
  4. customdried in vacuo
  5. customThe crude was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-3d0bdbc4b6fb4dda84c537483a6d7abb
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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