1,2-Dichloroethane → (+/-)-2-(Piperidin-1-ylcarbonyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1623089Notes

Reaction equation

HRID 1623089 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:25][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[C:18]([C:22](O)=[O:23])[CH:17]=[CH:16]3.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[N:26]1([C:22]([C:18]2[CH:17]=[CH:16][C:15]3[C:20](=[CH:21][C:12]4[CH2:11][C:3]5([C:4]6[C:5](=[N:6][CH:7]=[CH:8][CH:9]=6)[NH:10][C:2]5=[O:1])[CH2:25][C:13]=4[CH:14]=3)[N:19]=2)=[O:23])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59594282HCID 59594282, compound2×

Product 1

HCID 46916862(+/-)-2-(Piperidin-1-ylcarbonyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (±)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-2-carboxylic acid (15 mg, 0.045 mmol, described in Intermediate 12), piperidine (0.009 mL, 0.091 mmol), EDC (26 mg, 0.14 mmol), HOBT (21 mg, 0.14 mmol), and N,N-diisopropylethylamine (0.039 mL, 0.23 mmol) was stirred in DMF (1 mL) at ambient temperature for 18 h. The reaction mixture was purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions were combined and concentrated to give the title compound. MS: m/z=399 (M+1). HRMS: m/z=399.1817; calculated m/z—399.1816 for C24H22N4O2.

Workup

  1. customThe reaction mixture was purified directly by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c4280cdd33194db2a9550f71890d5c8d
Source dataset
uspto-grants-2014_07
Patent number
US08778957B2

Reaction notes

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