HCID 67027520, compound → HCID 58266647, compound

HRID 1506006Notes

Reaction equation

HRID 1506006 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]>C(N)CN>[NH2:10][CH2:11][CH2:12][NH:13][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[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]5)=[CH:20][CH:19]=4)=[CH:17][C:8]=3[C:7]=2[CH:6]=1)=[O:4]

Participants

3

Reactant 1

HCID 67027520HCID 67027520, compound

Product 1

HCID 58266647HCID 58266647, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 3301EthylenediamineSolvent

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 ethylenediamine (8.0 mL) was heated to 80° C. for 16 h in a sealed tube. The mixture was allowed to cool and concentrated in vacuo. The residue was dissolved in DMSO and purified by preparative HPLC (2-60% MeCN/water modified with 0.1% ammonium hydroxide) to afford a light brown solid (45.4 mg, 28%). 1H NMR (DMSO-D6, 400 MHz): 9.19 (d, J=2.1 Hz, 1H), 8.99 (s, 1H), 8.96 (d, J=2.2 Hz, 1H), 8.92 (s, 1H), 8.74 (m, 1H), 7.80 (d, J=8.1 Hz, 2H), 7.45 (d, J=8.1 Hz, 2H), 3.50 (s, 2H), 3.41-3.33 (m, 2H), 2.76 (t, J=6.4 Hz, 2H), 2.38 (m, 4H), 1.52 (m, 4H), 1.41 (m, 2H). LCMS (Method D): RT=6.45 min, M+H+=429.

Workup

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

Sources & evidence

ORD record
ord-25c3409e36cb413082f2779cc18eb5a8
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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