Morpholine → HCID 71525560, compound

HRID 1777792Notes

Reaction equation

HRID 1777792 reaction equation
Br[C:2]1[N:7]2[C:8](=[O:25])[N:9]([CH2:11][CH2:12][C:13]3[N:14]([CH3:24])[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:17]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[CH3:24][N:14]1[CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=[C:13]1[CH2:12][CH2:11][N:9]1[C:8](=[O:25])[N:7]2[C:2]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:3][CH:4]=[CH:5][C:6]2=[N:10]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 71571783HCID 71571783, compound

Product 1

HCID 71525560HCID 71525560, compoundYield 32%

Conditions

Temperature
120 °C

Procedure

In a 2 mL microwave vial were placed 11-4 (0.025 g, 0.063 mmol) and morpholine (0.459 g, 0.461 mL, 5.27 mmol). The vial was sealed and heated in an oil bath for 15 min at 120° C. The mixture was concentrated in vacuo and purified by reverse phase HPLC (5-50% MeCN/water with 0.01% TFA additive). Fractions containing pure product were treated with sat. aq. NaHCO3 and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, and filtered. The filtrate was dried under reduced pressure to give 8 mg (32%) of 12-1. LC/MS: m/z (M+H)=405.5. 1H NMR (500 MHz, CHCl3-d): δ 7.68 (d, J=7.7 Hz, 2H), 7.31 (d, J=7.6 Hz, 2H), 7.21-7.16 (m, 1H), 7.08 (s, 1H), 6.91 (dd, J=9.3, 7.0 Hz, 1H), 6.68 (d, J=9.3 Hz, 1H), 5.60 (d, J=7.3 Hz, 1H), 4.37 (t, J=7.5 Hz, 2H), 3.90-3.86 (m, 4H), 3.74-3.70 (m, 2H), 3.64 (s, 3H), 3.21 (t, J=7.5 Hz, 2H), 2.96-2.87 (m, 2H). HRMS (ES) 405.2048 found (M+H), 405.2035 required.

Workup

  1. customThe vial was sealed
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by reverse phase HPLC (5-50% MeCN/water with 0.01% TFA additive)
  4. additionFractions containing pure product
  5. additionwere treated with sat. aq. NaHCO3
  6. extractionextracted with EtOAc
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customThe filtrate was dried under reduced pressure

Sources & evidence

ORD record
ord-7a437ec19ef84c34871a38654b7f0bd2
Source dataset
uspto-grants-2016_02
Patent number
US09266881B2

Reaction notes

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