1,2-Dichloroethane → HCID 57663738, compound

HRID 551099Notes

Reaction equation

HRID 551099 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[C:36]2[C:37]3[CH:28]([CH2:29][C:30](=[O:38])[NH:31][C:32]=3[CH:33]=[CH:34][CH:35]=2)[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>[O:38]=[C:30]1[CH2:29][CH:28]2[CH2:27][N:26]([C:22]([C:18]3[CH:17]=[CH:16][C:15]4[C:20](=[CH:21][C:12]5[CH2:11][C@:3]6([C:4]7[C:5](=[N:6][CH:7]=[CH:8][CH:9]=7)[NH:10][C:2]6=[O:1])[CH2:25][C:13]=5[CH:14]=4)[N:19]=3)=[O:23])[C:36]3[C:37]2=[C:32]([CH:33]=[CH:34][CH:35]=3)[NH:31]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 104421921,2,2a,5-Tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-oneHCID 59594306HCID 59594306, compound2×

Product 1

HCID 57663738HCID 57663738, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-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 14), 1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one, enantiomer B (8 mg, 0.045 mmol, described in Intermediate 19), EDC (13 mg, 0.068 mmol), HOBT (9 mg, 0.068 mmol), and N,N-diisopropylethylamine (0.039 mL, 0.226 mmol) was stirred in DMF (0.7 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=488 (M+1). HRMS: m/z=488.1703; calculated m/z=488.1717 for C29H22N5O3.

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-e4d7c7a8fca3490db502f8fbc78951c4
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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