Ethylamine → HCID 58266536, compound

HRID 1506005Notes

Reaction equation

HRID 1506005 reaction equation
CO[C:3]([C:5]1[N:13]=[CH:12][C:11]2[NH:10][C:9]3[N:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24][N:25]5[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]5)=[CH:20][CH:19]=4)=[CH:17][C:8]=3[C:7]=2[CH:6]=1)=[O:4].[CH2:31]([NH2:33])[CH3:32]>C1COCC1>[CH2:31]([NH:33][C:3]([C:5]1[N:13]=[CH:12][C:11]2[NH:10][C:9]3[N:14]=[CH:15][C:16]([C:18]4[CH:19]=[CH:20][C:21]([CH2:24][N:25]5[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]5)=[CH:22][CH:23]=4)=[CH:17][C:8]=3[C:7]=2[CH:6]=1)=[O:4])[CH3:32]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 67027520HCID 67027520, compound

Product 1

HCID 58266536HCID 58266536, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-piperidin-1-ylmethyl-phenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester (152 mg, 0.380 mmol) in 2M ethylamine in THF (8.0 mL) was heated to 80° C. for 4 days in a sealed tube. The mixture was allowed to cool and concentrated in vacuo. The residue was redissolved in DMSO and purified by preparative HPLC [2-60% MeCN/water modified with 0.1% ammonium hydroxide] to afford a dark brown solid (74.9 mg, 48%). 1H NMR (DMSO-D6, 500 MHz): 9.19 (d, J=2.2 Hz, 1H), 8.99 (s, 1H), 8.97 (d, J=2.2 Hz, 1H), 8.91 (s, 1H), 8.72 (m, 1H), 8.24 (s, 1H), 7.81 (d, J=8.1 Hz, 2H), 7.45 (d, J=8.1 Hz, 2H), 3.47-3.33 (m, 2H), 2.38 (m, 4H), 1.53 (m, 4H), 1.42 (m, 2H), 1.18 (t, J=7.2 Hz, 3H). LCMS (Method E): RT=3.30 min, M+H+=414.

Workup

  1. temperatureto cool
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was redissolved in DMSO
  4. custompurified by preparative HPLC [2-60% MeCN/water modified with 0.1% ammonium hydroxide]

Sources & evidence

ORD record
ord-2f80224a12a24200b5867aca829ccf80
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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