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

HRID 656844Notes

Reaction equation

HRID 656844 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]([OH:24])=O)[CH:17]=[CH:16]3.[CH2:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][NH:27]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH2:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][N:27]1[C:22]([C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][C:12]3[CH2:11][C:3]4([C:4]5[C:5](=[N:6][CH:7]=[CH:8][CH:9]=5)[NH:10][C:2]4=[O:1])[CH2:25][C:13]=3[CH:14]=2)[N:19]=1)=[O:24]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 422478IsoindolineHCID 59594282HCID 59594282, compound2×

Product 1

HCID 17757605(+/-)-2-(1,3-Dihydro-2H-isoindol-2-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 (10 mg, 0.030 mmol, described in Intermediate 19), isoindoline (7 mg, 0.060 mmol), EDC (9 mg, 0.045 mmol), HOBT (7 mg, 0.045 mmol), and N,N-diisopropylethylamine (0.026 mL, 0.151 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:CH3 CN:CF3 CO2H—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=433 (M+1). HRMS: m/z=433.1667; calculated m/z=433.1659 for C27H21N4O2.

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-12e79f1c34da46daa20a718b11722c0d
Source dataset
uspto-grants-2011_12
Patent number
US08071772B2

Reaction notes

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