Morpholine → HCID 178521237, compound

HRID 1483845Notes

Reaction equation

HRID 1483845 reaction equation
Cl[CH2:2][C:3]([NH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)=[CH:20][N:21]=3)[N:18]=2)[CH2:8][CH2:7]1)=[O:4].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:28][C:24]1[CH:23]=[C:22]([C:19]2[N:17]3[N:18]=[C:13]([NH:12][C@H:9]4[CH2:10][CH2:11][C@H:6]([NH:5][C:3](=[O:4])[CH2:2][N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)[CH2:7][CH2:8]4)[CH:14]=[CH:15][C:16]3=[N:21][CH:20]=2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 178520812HCID 178520812, compound

Product 1

HCID 178521237HCID 178521237, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-chloro-N-(trans-4-((3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexyl)acetamide (50 mg, 0.12 mmol), morpholine (0.3 mL) and DIPEA (0.2 mL) in CH2Cl2 (0.6 mL) was stirred at 50° C. for 3 h. LCMS showed the reaction was complete. The mixture was concentrated in vacuo. The residue was partitioned between water (100 mL) and EtOAc (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-HPLC to give EX. 8-84 (9.6 mg, 17%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was partitioned between water (100 mL) and EtOAc (50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by prep-HPLC
  7. customto give EX

Sources & evidence

ORD record
ord-dfb83d5cc2184517a79c4b53301bf8e2
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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