Ammonia → HCID 58266373, compound

HRID 1506004Notes

Reaction equation

HRID 1506004 reaction equation
C[O:2][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.[NH3:31]>CO>[N:25]1([CH2:24][C:21]2[CH:22]=[CH:23][C:18]([C:16]3[CH:15]=[N:14][C:9]4[NH:10][C:11]5[CH:12]=[N:13][C:5]([C:3]([NH2:31])=[O:2])=[CH:6][C:7]=5[C:8]=4[CH:17]=3)=[CH:19][CH:20]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67027520HCID 67027520, compound

Product 1

HCID 58266373HCID 58266373, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(4-piperidin-1-ylmethyl-phenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester (67.3 mg, 0.168 mmol) in 7M ammonia in methanol (8.0 mL) was heated to 70° C. for 24 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-yellow fluffy solid (10.3 mg, 16%). 1H NMR (DMSO-D6, 500 MHz): 12.56 (s, 1H), 9.18 (d, J=2.2 Hz, 1H), 9.00 (s, 1H), 8.96 (d, J=2.1 Hz, 1H), 8.90 (s, 1H), 8.10 (s, 1H), 7.79 (d, J=8.1 Hz, 2H), 7.53 (s, 1H), 7.44 (d, J=8.1 Hz, 2H), 3.49 (s, 2H), 2.36 (m, 4H), 1.56-1.47 (m, 4H), 1.40 (m, 2H). LCMS (Method D): RT=5.88 min, M+H+=386.

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-655293dbd1cf4966a3f385614e086a37
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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