Dimethylamine → HCID 71293455, compound

HRID 570887Notes

Reaction equation

HRID 570887 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:31])[N:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29]Br)=[CH:25][CH:24]=3)[N:21]=[C:8]2[N:7]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=2)[C:6]=1[CH3:42])=[O:4].[CH3:43][NH:44][CH3:45]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:31])[N:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][N:44]([CH3:45])[CH3:43])=[CH:25][CH:24]=3)[N:21]=[C:8]2[N:7]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=2)[C:6]=1[CH3:42])=[O:4]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86678225HCID 86678225, compound

Product 1

HCID 71293455HCID 71293455, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 15 (105 mg, 0.16 mmol) was dissolved in THF (3 ml), and then dimethylamine (2 M in THF, 400 μl, 0.8 mmol) was added. The reaction mixture was stirred at RT for 16 hours and then filtered. The filtrate was collected and concentrated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 5-8% MeOH in DCM and gave the title compound as a white solid (72 mg).

Workup

  1. filtrationfiltered
  2. customThe filtrate was collected
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by silica gel chromatography
  5. washeluting with a gradient of 5-8% MeOH in DCM

Sources & evidence

ORD record
ord-e99009402958410bb6d33490e43e2973
Source dataset
uspto-grants-2015_05
Patent number
US09023855B2

Reaction notes

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