4-Methylmorpholine → HCID 16734977, compound

HRID 2262853Notes

Reaction equation

HRID 2262853 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([F:33])[CH:32]=1)[CH2:5][NH:6][CH2:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]1[CH2:18][C:19]3([CH2:29][C:13]=1[CH:12]=2)[C:27]1[C:22](=[N:23][CH:24]=[CH:25][CH:26]=1)[NH:21][C:20]3=[O:28].CN1CCOCC1.[CH3:41][C:42]([CH3:47])([CH3:46])[C:43](Cl)=[O:44]>C(Cl)Cl.CN1CCOCC1>[F:33][C:31]1[CH:30]=[C:4]([CH:3]=[C:2]([F:1])[CH:32]=1)[CH2:5][N:6]([CH2:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]1[CH2:18][C:19]3([CH2:29][C:13]=1[CH:12]=2)[C:27]1[C:22](=[N:23][CH:24]=[CH:25][CH:26]=1)[NH:21][C:20]3=[O:28])[C:43](=[O:44])[C:42]([CH3:47])([CH3:46])[CH3:41]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 62493Pivaloyl chloride2×HCID 68676101HCID 68676101, compound

Product 1

HCID 16734977HCID 16734977, compound

Reagents, catalysts & solvents 2

HCID 79724-MethylmorpholineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (±)-3-{[(3,5-difluorobenzyl)amino]methyl}-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step A (47.0 mg, 0.106 mmol) in DCM (1.5 mL) was added 4-methylmorpholine (32.2 mg, 0.320 mmol). This mixture was sonicated to provided a finely powdered suspension. After cooling to 0° C., trimethylacetyl chloride (23.0 mg, 0.190 mmol) was added and the cooling bath was removed. After 23 hours, additional 4methylmorpholine (2 drops) and trimethylacetyl chloride (23.0 mg, 0.190 mmol) were added. After 7 hours, the reaction was quenched by the addition of one drop of methanol. This reaction mixture was applied to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH—100:1 to 94:6, to give the title compound as a white solid. MS: m/z=527 (M+1). HRMS: m/z=527.2253; calculated m/z=527.2253 for C31H29F2N4O2.

Workup

  1. customThis mixture was sonicated
  2. customto provided a finely powdered suspension
  3. customthe cooling bath was removed
  4. waitAfter 7 hours
  5. customthe reaction was quenched by the addition of one drop of methanol
  6. customThis reaction mixture was applied to a silica gel column for purification
  7. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-ab0ca2abaf254f0bb6793b54a77b2eb8
Source dataset
uspto-grants-2010_12
Patent number
US07851464B2

Reaction notes

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