Morpholine → HCID 23729275, compound

HRID 1911775Notes

Reaction equation

HRID 1911775 reaction equation
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:6][N:7]([CH2:15][C:16]1[C:17]([N:27]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH2:28][CH:29]2[CH2:31][CH2:30]2)=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:26])[C:8]1[N:13]=[C:12](Cl)[N:11]=[CH:10][N:9]=1.C(N(C(C)C)CC)(C)C.[NH:54]1[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1>CN(C=O)C.CCOC(C)=O>[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:6][N:7]([CH2:15][C:16]1[C:17]([N:27]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH2:28][CH:29]2[CH2:31][CH2:30]2)=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:26])[C:8]1[N:13]=[C:12]([N:54]2[CH2:59][CH2:58][O:57][CH2:56][CH2:55]2)[N:11]=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 23729274HCID 23729274, compound

Product 1

HCID 23729275HCID 23729275, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (3-{[(3,5-bis-trifluoromethyl-benzyl)-(4-chloro-[1,3,5]triazin-2-yl)-amino]methyl}-8-methyl-quinolin-2-yl)-bis-cyclopropylmethyl-amine (Example 117) (60 mg, 0.09 mmol), diisopropyl ethylamine (13 μL, 0.1 mmol) was taken in DMF (10 mL). The flask was cooled to 0° C. and the contents were stirred for 5 min. To this, morpholine (12 μL, 0.13 mmol) was added and the stirring was continued for 30 min at 0° C. and then warming up to room temperature. Contents of the flask were taken in 100 mL EtOAc and washed with water (100 mL×3). The organic layer was separated, dried over sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography; (silica gel 230-400 mesh). Elution with 2% EtOAc in hexane afforded 58 mg of colorless mass (yield: 78%).

Workup

  1. waitthe stirring was continued for 30 min at 0° C.
  2. temperaturewarming up to room temperature
  3. washwashed with water (100 mL×3)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by column chromatography
  8. washElution with 2% EtOAc in hexane
  9. customafforded 58 mg of colorless mass (yield: 78%)

Sources & evidence

ORD record
ord-ce9fca4f65024492a4a6e247de40afe6
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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