Triethylamine → HCID 58266409, compound

HRID 1505987Notes

Reaction equation

HRID 1505987 reaction equation
C1(S([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:28]#[N:29])=[C:18]([CH2:19][CH:20]4[CH2:25][CH2:24][N:23]([CH2:26][CH3:27])[CH2:22][CH2:21]4)[C:13]=3[C:12]3[CH:30]=[CH:31][CH:32]=[N:33][C:11]2=3)(=O)=O)C=CC=CC=1.C(N(CC)CC)C>CO>[CH2:26]([N:23]1[CH2:24][CH2:25][CH:20]([CH2:19][C:18]2[C:13]3[C:12]4[CH:30]=[CH:31][CH:32]=[N:33][C:11]=4[NH:10][C:14]=3[CH:15]=[N:16][C:17]=2[C:28]#[N:29])[CH2:21][CH2:22]1)[CH3:27]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 58266442HCID 58266442, compound

Product 1

HCID 58266409HCID 58266409, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 9-benzenesulfonyl-5-(1-ethyl-piperidin-4-ylmethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (200 mg, 0.4 mmol) and triethylamine (4 mL) in methanol (40 mL) was stirred at ambient temperature for 6 days. The mixture was concentrated in vacuo and the residue purified by flash chromatography (silica, 2 g column, Si-SPE, 0-20% MeOH in DCM). The resultant material was triturated with acetonitrile and methanol to afford the title compound as a white solid (65 mg, 51%). 1H NMR (DMSO-D6, 400 MHz): 12.85 (s, 1H), 8.90 (s, 1H), 8.70 (dd, J=4.8, 1.5 Hz, 1H), 8.65 (dd, J=8.0, 1.6 Hz, 1H), 7.46 (dd, J=8.0, 4.8 Hz, 1H), 2.86-2.77 (m, 2H), 2.24 (q, J=7.2 Hz, 2H), 1.84-1.58 (m, 5H), 1.54-1.40 (m, 2H), 0.95 (t, J=7.1 Hz, 3H). LCMS (Method H): RT=4.56 min, M+H+=320.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by flash chromatography (silica, 2 g column, Si-SPE, 0-20% MeOH in DCM)
  3. customThe resultant material was triturated with acetonitrile and methanol

Sources & evidence

ORD record
ord-542f3b09905f4af794176679bd3a7833
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

Loading…