Morpholine → HCID 71571666, compound

HRID 1777784Notes

Reaction equation

HRID 1777784 reaction equation
Br[C:2]1[N:7]2[C:8](=[O:23])[N:9]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[O:27]1[CH2:28][CH2:29][N:24]([C:2]2[N:7]3[C:8](=[O:23])[N:9]([CH2:11][CH2:12][C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 71573383HCID 71573383, compound

Product 1

HCID 71571666HCID 71571666, compoundYield 85%

Conditions

Temperature
120 °C

Procedure

In a 5 mL microwave vial was placed 2-4 (221 mg, 0.599 mmol) and morpholine (2.0 g, 2.0 mL, 23 mmol). The mixture was heated at 120° C. under microwave irradiation for 20 min. After cooling, the reaction mixture was purified by reversed phase HPLC to give 191 mg (85%) of 6-1. 1H NMR (500 MHz, DMSO-d6): δ 8.51 (d, J=8.2 Hz, 1H), 8.05 (d, J=8.2 Hz, 1H), 7.96 (d, J=8.5 Hz, 1H), 7.83 (t, J=7.7 Hz, 1H), 7.69-7.60 (m, 2H), 7.00 (t, J=8.1 Hz, 1H), 6.67 (d, J=9.3 Hz, 1H), 5.72 (d, J=7.0 Hz, 1H), 4.32 (t, J=7.0 Hz, 2H), 3.63 (m, 4H), 3.10 (s, 1H), 2.99 (s, 1H), 2.93 (s, 4H). HRMS (ES) 376.1765 (M+H) found, 376.1771 required.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-fbb0c54be88540f4b9f26d3ce1920707
Source dataset
uspto-grants-2016_02
Patent number
US09266881B2

Reaction notes

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