N-Methylallylamine → HCID 89662809, compound

HRID 1479111Notes

Reaction equation

HRID 1479111 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[N:9][C:8]2[N:4]([N:5]=[C:6]3[CH2:14][N:13]([C:15]([C:17]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:18]=4[O:19][CH2:20][C:21](=O)[CH3:22])=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:29].[CH2:30]([NH:33][CH3:34])[CH:31]=[CH2:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CC(=O)OCC>[CH2:30]([N:33]([CH3:34])[CH:21]([CH3:22])[CH2:20][O:19][C:18]1[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:17]=1[C:15]([N:13]1[CH2:12][C:7]2=[C:8]3[N:4]([N:5]=[C:6]2[CH2:14]1)[C:3]([CH3:29])=[C:2]([Cl:1])[C:10]([CH3:11])=[N:9]3)=[O:16])[CH:31]=[CH2:32]

Participants

6

Reactant 3

HCID 69391N-MethylallylamineHCID 5049666Sodium triacetoxyborohydrideHCID 89662835HCID 89662835, compound

Product 1

HCID 89662809HCID 89662809, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 164 (150 mg; 0.36 mmol; 1 eq.) allyl-methyl-amine (51 mg; 0.72 mmol; 2 eq.) and sodium triacetoxyborohydride (99 mg; 0.47 mmol; 1.3 eq.) in DCE (5 mL) was stirred at 70° C. for 2 hours. The suspension was diluted with EA, washed with water, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (EA to 12% MeOH in EA) afforded the title compound (95 mg, 56%) as a white solid. 1H NMR (DMSO-d6) δ 7.45-7.29 (m, 1H), 7.17-7.02 (m, 1H), 6.87 (td, J=8.5, 2.4 Hz, 1H), 5.57-5.37 (m, 1H), 4.92 (dd, J=16.8, 5.8 Hz, 1H), 4.86-4.71 (m, 3H), 4.70-4.46 (m, 2H), 4.13-3.90 (m, 2H), 3.09-2.89 (m, 3H), 2.84 (s, 1.6H), 2.80 (s, 1.4H), 2.61 (s, 1.4H), 2.55 (s, 1.6H), 2.02 (d, J=4.9 Hz, 3H), 0.88 (dd, J=6.5, 1.9 Hz, 3H). HPLC (max plot) 94.9%, Rt 2.97 min. UPLC/MS: (MS+) 472.2 ([M+H]+).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (EA to 12% MeOH in EA)

Sources & evidence

ORD record
ord-4b85b448e8e441f190875bff73901ed3
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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