4-(Morpholinomethyl)aniline → HCID 68195256, compound

HRID 2370630Notes

Reaction equation

HRID 2370630 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.[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)[CH2:27][CH2:26]1>>[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:36][C:35]3[CH:34]=[CH:33][C:32]([CH2:31][N:28]4[CH2:27][CH2:26][O:25][CH2:30][CH2:29]4)=[CH:38][CH:37]=3)=[N:12][C:11]=2[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12

Participants

3

Reactant 2

HCID 7768514-(Morpholinomethyl)anilineHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Product 1

HCID 68195256HCID 68195256, compound

Procedure

A mixture of Example 1E (0.060 g, 0.167 mmol) and 4-(morpholinomethyl)aniline (0.051 g, 0.267 mmol) was heated in a capped vial at 90° C. for 1 hour. The crude material was purified by HPLC (see protocol in Example 1F). The TFA salt was treated with saturated aqueous NaHCO3 and extracted into ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated, and 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 2.56-2.39 (m, 4H), 3.54 (s, 2H), 3.73-3.67 (m, 4H), 7.05 (d, J=1.9 Hz, 1H), 7.43-7.36 (m, 2H), 7.61-7.52 (m, 3H), 7.70-7.67 (m, 1H), 7.80-7.73 (m, 2H), 7.86 (s, 1H), 9.15 (s, 1H). MS (ESI+) m/z 488.0 (M+H)+.

Workup

  1. customThe crude material was purified by HPLC (see protocol in Example 1F)
  2. additionThe TFA salt was treated with saturated aqueous NaHCO3
  3. extractionextracted into ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on a 12 g column
  8. washeluting with methanol/ethyl acetate (5:95 to 10:90)

Sources & evidence

ORD record
ord-f1f8fdd0c25c4825a3bf3d540ee9e929
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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