Dimethylamine → HCID 89662837, compound

HRID 1479112Notes

Reaction equation

HRID 1479112 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].[CH3:30][NH:31][CH3:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>C1COCC1.ClCCCl.C(OCC)(=O)C>[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][CH:21]([N:31]([CH3:32])[CH3:30])[CH3:22])=[O:16])[CH2:12][C:7]3=2)[C:3]=1[CH3:29]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 2724942TriacetoxyborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 89662835HCID 89662835, compound

Product 1

HCID 89662837HCID 89662837, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of Example 164 (90 mg; 0.22 mmol; 1 eq.), a 2M solution of dimethylamine in THF and sodium triacetoxyborohydride (59 mg; 0.28 mmol; 1.3 eq.) in DCE (2 mL) was stirred at 50° C. for 1 hour whereupon triacetoxyborohydride (59 mg; 0.28 mmol; 1.3 eq.) was added. The resulting mixture was stirred at 70° C. for 3 hours then diluted with ethyl acetate. The solution was washed with 0.1M NaOH, dried over sodium sulfate and concentrated in vacuo. Purification by column chromatography (EA to 10 MeOH in EA) afforded the title compound (27 mg, 28%) as a white solid. 1H NMR (DMSO-d6) δ 7.42-7.26 (m, 1H), 7.09 (d, J=11.5 Hz, 1H), 6.86 (t, J=8.2 Hz, 1H), 4.78 (d, J=7.9 Hz, 2H), 4.59 (d, J=15.0 Hz, 2H), 4.13-3.89 (m, 2H), 2.92-2.74 (m, 4H), 2.61 (s, 1.4H), 2.56 (s, 1.6H), 2.06 (s, 6H), 0.95-0.78 (m, 3H). HPLC (max plot) 99.9%, Rt 2.77 min. UPLC/MS: (MS+) 446.3 ([M+H]+).

Workup

  1. additionwas added
  2. washThe solution was washed with 0.1M NaOH
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (EA to 10 MeOH in EA)

Sources & evidence

ORD record
ord-e79b0272ce6b45ee90e259b609cc3b02
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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