Morpholine → HCID 86271202, compound

HRID 528000Notes

Reaction equation

HRID 528000 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:15][CH:16]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(N(C(C)C)C(C)C)C>O1CCCC1>[CH3:20][S:17]([N:14]1[CH2:15][CH:16]=[C:11]([C:9]2[NH:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[C:3]=3[CH:10]=2)[CH2:12][CH2:13]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 90418872HCID 90418872, compound

Product 1

HCID 86271202HCID 86271202, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Example 41A (100 mg, 0.320 mmol) and morpholine (2.52 mL, 3 mmol) in 3 mL tetrahydrofuran/1 mL N,N-dimethylformamide was added N-ethyl-N-isopropylpropan-2-amine (0.084 mL, 0.480 mmol). The resulting reaction was stirred at 60° C. overnight. The solvent was removed in vacuo and the residue dried under high-vacuum for 2 hours. The crude solid was triturated with ethyl acetate, collected by filtration, and dried under high-vacuum to give the title compound. 1H NMR (500 MHz, DMSO-d6) δ 11.93 (s, 1H) 8.17 (s, 1H) 6.68 (s, 1H) 6.41 (s, 1H) 3.66-3.93 (m, 8H) 3.37 (t, J=5.65 Hz, 2H) 3.02-3.12 (m, 2H) 2.89-2.98 (m, 3H) 2.62 (s, 2H). MS (ESI+) m/z 364.2 (M+H)+.

Workup

  1. customThe resulting reaction
  2. customThe solvent was removed in vacuo
  3. customthe residue dried under high-vacuum for 2 hours
  4. customThe crude solid was triturated with ethyl acetate
  5. filtrationcollected by filtration
  6. customdried under high-vacuum

Sources & evidence

ORD record
ord-996a5e6c93fb4a12b0336e163cd739f4
Source dataset
uspto-grants-2016_05
Patent number
US09346813B2

Reaction notes

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