Cyclopentanecarboxylic acid → HCID 90410963, compound

HRID 2175743Notes

Reaction equation

HRID 2175743 reaction equation
CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O.[Br:17][C:18]1[CH:19]=[C:20]2[C:30](=[N:31][CH:32]=1)[NH:29][C:28](=[O:33])[C:22]1([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH2:21]2.[CH:34]1([C:39](O)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[Br:17][C:18]1[CH:19]=[C:20]2[C:30](=[N:31][CH:32]=1)[NH:29][C:28](=[O:33])[C:22]1([CH2:27][CH2:26][N:25]([C:39]([CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:40])[CH2:24][CH2:23]1)[CH2:21]2

Participants

7

Reactant 5

HCID 18840Cyclopentanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 90135746HCID 90135746, compound

Product 1

HCID 90410963HCID 90410963, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

DIPEA (1.22 mL, 8.82 mmol) was added to a stirred solution of 6-bromo-1H-spiro[[1,8]naphthyridine-3,4′-piperidin]-2(4H)-one 2,2,2-trifluoroacetate (Intermediate-14) (600 mg, 1.47 mmol), cyclopentanecarboxylic acid (250 mg, 2.20 mmol), HOBt (390 mg, 2.94 mmol) and EDC.HCl (700 mg, 3.67 mmol) in dry DMF (5 mL) at 20-35° C. and the reaction mixture was allowed to stir at 20-35° C. for 16 h. Then the reaction mixture was poured into ice water (100 mL), obtained solid was filtered, washed with water and dried under vacuum to get the desired compound as an off-white solid (250 mg, 43%); 1H NMR (400 MHz, DMSO-d6) δ 10.74 (s, 1H), 8.23 (d, J=2.0 Hz, 1H), 7.86 (d, J=1.9 Hz, 1H), 3.76-3.67 (m, 3H), 3.47-3.41 (m, 1H), 2.99 (s, 2H), 2.96-2.94 (m, 1H), 1.90-1.72 (m, 4H), 1.71-1.56 (m, 4H), 1.55-1.42 (m, 2H), 1.38-1.23 (m, 2H).

Workup

  1. customobtained solid
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-104d31eacf1e49d896d361f562a2d728
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

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