Diisopropylethylamine → HCID 178425377, compound

HRID 2409486Notes

Reaction equation

HRID 2409486 reaction equation
Cl[C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:12]([N:28]=1)=[CH:13][C:14]1[CH2:15][N:16]([CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[C:17](=[O:20])[C:18]=1[CH:19]=2.[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:40])=[C:34]([CH2:36][C@@H:37]([NH2:39])[CH3:38])[CH:35]=1.CCN(C(C)C)C(C)C>CCO>[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:40])=[C:34]([CH2:36][C@@H:37]([NH:39][C:2]2[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=2[C:9]2[NH:10][C:11]3[C:12]([N:28]=2)=[CH:13][C:14]2[CH2:15][N:16]([CH2:21][CH2:22][N:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)[C:17](=[O:20])[C:18]=2[CH:19]=3)[CH3:38])[CH:35]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86677133HCID 86677133, compoundHCID 178514857HCID 178514857, compound

Product 1

HCID 178425377HCID 178425377, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-(2-pyrrolidin-1-ylethyl)-6,7-dihydroimidazo[4,5-f]isoindol-5(3H)-one (50 mg, 0.126 mmol), (1S)-2-(5-chloro-2-methylphenyl)-1-methylethylamine (30 mg, 0.164 mmol) and DIEA (66 uL, 0.38 mmol) in 2 mL of EtOH was heated at 80° C. for 24 h. Then the solvent was evaporated and the residue was purified by column (silica gel, DCM:MeOH 95:5) to give 2-(4-((1S)-2-(5-cloro-2-methylphenyl)-1-methylethylamino)-2-oxo-1,2-dihydropyridin-3-yl)-6-(2-pyrrolidin-1-ylethyl)-6,7-dihydroimidazo[4,5-f]isoindol-5(3H)-one (41 mg, 59%) as yellow solid. ESI-MS: m/z (MH+) 545.5. 1H NMR (300 MHz, CDCl3): δ 7.96 (d, J=44.8 Hz, 1H), 7.51 (d, J=66.3 Hz, 1H), 7.20 (m, 2H), 7.03 (m, 2H), 5.86 (m, 1H), 4.59 (m, 2H), 3.93 (m, 3H), 2.96-3.13 (m, 8H), 2.32 (s, 3H), 1.91 (m, 4H), 1.38 (d, J=7.35 Hz, 3H).

Workup

  1. customThen the solvent was evaporated
  2. customthe residue was purified by column (silica gel, DCM:MeOH 95:5)

Sources & evidence

ORD record
ord-f7048c1fd67c4001a84542900decb3d0
Source dataset
uspto-grants-2014_08
Patent number
US08815906B2

Reaction notes

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