Cyclopentylamine → 4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline-7-carboxylic Acid Cyclopentylamide

HRID 8256

Reaction equation

HRID 8256 reaction equation
Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1.[CH:23]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24]1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]1[C:36]([C:43]2[C:52]3[C:47](=[CH:48][C:49]([C:53](O)=[O:54])=[CH:50][CH:51]=3)[N:46]=[CH:45][CH:44]=2)=[C:37]2[CH2:42][CH2:41][CH2:40][N:38]2[N:39]=1>ClCCl>[CH:23]1([NH:28][C:53]([C:49]2[CH:48]=[C:47]3[C:52]([C:43]([C:36]4[C:35]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=5)=[N:39][N:38]5[CH2:40][CH2:41][CH2:42][C:37]=45)=[CH:44][CH:45]=[N:46]3)=[CH:51][CH:50]=2)=[O:54])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219924874-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline-7-carboxylic Acid

Product 1

HCID 101371304-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline-7-carboxylic Acid Cyclopentylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, (53 mg, 0.30 mmol), HOBT, (24 mg, 0.28 mmol), cyclopentylamine (0.03 mL, 0.30 mmol), and 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline-7-carboxylic acid (90 mg, 0.25 mmol) in dichloromethane (1 mL) is stirred room temperature for 18 h. The mixture is concentrated in vacuo and the residue chromatographed on SiO2 to yield the title compound, 31 mg (31%,) as a white solid.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe residue chromatographed on SiO2

Sources & evidence

ORD record
ord-7e43ca3ac0294abfb9cc8c732e641078
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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