Morpholine → HCID 54576906, compound

HRID 1777713Notes

Reaction equation

HRID 1777713 reaction equation
[CH2:1]([N:8]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][CH:21]=[N:22]3)=[C:17](Cl)[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>>[CH2:1]([N:8]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][CH:21]=[N:22]3)=[C:17]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 86682418HCID 86682418, compound

Product 1

HCID 54576906HCID 54576906, compound

Procedure

A solution of dibenzyl-[4-(5-chloro-[1,6]naphthyridin-7-yl)-phenyl]amine 3 (350 mg, 0.81 mmol, 1 eq) in morpholine (5.0 mL, 56 mmol, 70 eq) was heated up at 100° C. overnight under Ar(g). Once cooled down, the solution was partitioned and extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1:1-1:3) to yield the product, B, as a pale yellow solid (242 mg, 62%).

Workup

  1. temperatureOnce cooled down
  2. customthe solution was partitioned
  3. extractionextracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was further purified by silica gel column chromatography with hexane/EtOAc (1:1-1:3)
  7. customto yield the product, B

Sources & evidence

ORD record
ord-abfe7d0fcfee48bd83513c8f18ad0784
Source dataset
uspto-grants-2016_02
Patent number
US09266879B2

Reaction notes

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