1,2-Dichloroethane → HCID 89582846, compound

HRID 1501246Notes

Reaction equation

HRID 1501246 reaction equation
[NH2:1][CH2:2][C:3]1[C:8](=[O:9])[NH:7][C:6]2[CH2:10][CH2:11][CH2:12][C:5]=2[C:4]=1C.[O:14]([C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[O:9]=[C:8]1[NH:7][C:6]2[CH2:10][CH2:11][CH2:12][C:5]=2[CH:4]=[C:3]1[CH2:2][NH:1][C:25](=[O:26])[C:24]1[CH:23]=[CH:22][C:21]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 751824-Phenoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 89582777HCID 89582777, compound

Product 1

HCID 89582846HCID 89582846, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a pyrex vial 3-(aminomethyl)-4-methyl-6,7-dihydro-1H-cyclopenta[b]pyridin-2(5H)-one (35 mg, 0.21 mmol), 4-phenoxybenzoic acid (50 mg, 0.23 mmol), HOBT (36 mg, 0.23 mmol) and DMF (1.5 mL) were cooled to 0° C. EDC (45 mg, 0.23 mmol) was then added in one portion and the cold bath was removed. The reaction was mixed at ambient temperature overnight then diluted with MeOH (2 mL) and water (1 mL), filtered through a PTFE screen and purified by reverse-phase HPLC 10-95% gradient of MeCN in water (0.1% TFA). The product fractions were lyophilized to produce N-((2-oxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridin-3-yl)methyl)-4-phenoxybenzamide as a white solid (43 mg, 56%). 1H NMR (400 MHz, DMSO-d6) δ 8.70 (t, J=5.71 Hz, 1H), 7.87-7.96 (m, 2H), 7.38-7.47 (m, 2H), 7.15-7.23 (m, 2H), 7.05-7.11 (m, 2H), 6.99-7.05 (m, 2H), 4.19 (d, J=5.61 Hz, 2H), 2.69 (t, J=7.48 Hz, 2H), 2.58 (t, J=7.17 Hz, 2H), 1.98 (quin, J=7.43 Hz, 1H). LRMS (M+H+) m/z: calcd 361.15. found 361.2.

Workup

  1. customthe cold bath was removed
  2. additionThe reaction was mixed at ambient temperature overnight
  3. additionthen diluted with MeOH (2 mL) and water (1 mL)
  4. filtrationfiltered through a PTFE screen
  5. custompurified by reverse-phase HPLC 10-95% gradient of MeCN in water (0.1% TFA)

Sources & evidence

ORD record
ord-d7b01eeb9a074e25be56f62ba4845d6a
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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