4-Imidazol-1-ylmethylphenylamine → HCID 68194559, compound

HRID 2370631Notes

Reaction equation

HRID 2370631 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13](S(C)=O)=[N:14][CH:15]=2)[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[N:25]1([CH2:30][C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)[CH:29]=[CH:28][N:27]=[CH:26]1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[CH:15]=[N:14][C:13]([NH:35][C:34]3[CH:33]=[CH:32][C:31]([CH2:30][N:25]4[CH:29]=[CH:28][N:27]=[CH:26]4)=[CH:37][CH:36]=3)=[N:12][C:11]=2[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12

Participants

4

Reactant 2

HCID 12653194-Imidazol-1-ylmethylphenylamineHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Product 1

HCID 68194559HCID 68194559, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 1E (0.060 g, 0.167 mmol) and 4-((1H-imidazol-1-yl)methyl)aniline (0.046 g, 0.267 mmol) was heated in a capped vial at 100° C. for 1 hour. The reaction mixture was treated with ethyl acetate and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, and concentrated. The crude material was purified on a 12 g column using the ISCO Companion flash system eluting with methanol/ethyl acetate (5:95 to 10:90) to provide the title compound. 1H NMR (400 MHz, CD3OD) δ 5.23 (s, 2H), 7.00 (s, 1H), 7.04 (d, J=1.9 Hz, 1H), 7.14 (s, 1H), 7.35-7.29 (m, 2H), 7.61-7.51 (m, 3H), 7.71-7.64 (m, 1H), 7.87-7.75 (m, 4H), 9.14 (s, 1H). MS (ESI+) m/z 468.8 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified on a 12 g column
  6. washeluting with methanol/ethyl acetate (5:95 to 10:90)

Sources & evidence

ORD record
ord-123be15ee4e141f58d244fe8d7840fab
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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