Morpholine → HCID 67464257, compound

HRID 1777716Notes

Reaction equation

HRID 1777716 reaction equation
[CH2:1]([N:8]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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][C:10]=1[C:26]([F:29])([F:28])[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>>[CH2:1]([N:8]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[N:16]=2)=[CH:11][C:10]=1[C:26]([F:29])([F:28])[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 86682419HCID 86682419, compound

Product 1

HCID 67464257HCID 67464257, compoundYield 26%

Procedure

A solution of dibenzyl-[4-(5-chloro-[1,6]naphthyridin-7-yl)-2-trifluoromethyl-phenyl]-amine, 3, (100 mg, 0.20 mmol, 1 eq) in morpholine (1.25 mL, 14 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 (1:3-0:1) to yield the product as a pale yellow solid (29.1 mg, 26%).

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 (1:3-0:1)

Sources & evidence

ORD record
ord-d5056199996c4ed2aa3daca0a1e7d093
Source dataset
uspto-grants-2016_02
Patent number
US09266879B2

Reaction notes

Loading…