Ammonium Hydroxide → HCID 90290175, compound

HRID 2170401Notes

Reaction equation

HRID 2170401 reaction equation
[Cl:1][C:2]1[C:3]([CH:9]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[N:4][CH:5]=[C:6](Cl)[N:7]=1.[OH-].[NH4+:28]>O1CCOCC1>[NH2:28][C:6]1[N:7]=[C:2]([Cl:1])[C:3]([CH:9]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 90290176HCID 90290176, compound

Product 1

HCID 90290175HCID 90290175, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

In a high pressure reaction vessel, a suspension of 59B (300 mg, 0.742 mmol) in dioxane (2 mL) was treated with ammonium hydroxide (28%) (3 mL) and heated at 90° C. overnight. Solvents were removed and the crude was purified by flash chromatography to provide the title compound: 1H NMR (400 MHz, methanol-d4) δ 8.17 (d, 1H), 7.33-6.97 (m, 2H), 6.84-6.31 (m, 4H), 5.25 (m, 1H), 4.65 (s, 1H), 3.42 (d, 2H), 3.27-2.96 (m, 6H), 2.47 (m, 2H), 1.38 (m, 1H), 1.05 (m, 1H). MS (m/z) 385 [M+H]+.

Workup

  1. customIn a high pressure reaction vessel
  2. customSolvents were removed
  3. customthe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-aebd88a24d4c43e7948d8fcf3a338b13
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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