Ammonium hydroxide methanol → HCID 89662742, compound

HRID 1479078Notes

Reaction equation

HRID 1479078 reaction equation
C([O:3][C:4](=O)[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([N:17]1[CH2:31][C:20]2=[C:21]3[N:26]([N:27]=[C:19]2[CH2:18]1)[C:25]([CH3:28])=[C:24]([Cl:29])[C:23]([CH3:30])=[N:22]3)=[O:16])([F:7])[F:6])C.[NH4+:33].[OH-].CO>>[Cl:29][C:24]1[C:23]([CH3:30])=[N:22][C:21]2[N:26]([N:27]=[C:19]3[CH2:18][N:17]([C:15]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[O:8][C:5]([F:6])([F:7])[C:4]([NH2:33])=[O:3])=[O:16])[CH2:31][C:20]3=2)[C:25]=1[CH3:28]

Participants

3

Reactant 2

HCID 21894508Ammonium hydroxide methanolHCID 89650618HCID 89650618, compound

Product 1

HCID 89662742HCID 89662742, compoundYield 38%

Procedure

To [2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxy]-difluoro-acetic acid ethyl ester (from example 102 step 1) (70 mg; 0.15 mmol; 1 eq.) was added NH4OH/MeOH and the reaction mixture was stirred at room temperature for 1.5 hour then concentrated in vacuo. The residue taken up in EA, washed sat. aq. NH4Cl, dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (25 mg, 38%) as a white solid. HPLC (max plot) 99.6%, Rt 3.28 min. UPLC/MS: (MS+) 436.4 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. washwashed sat. aq. NH4Cl
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by mass

Sources & evidence

ORD record
ord-eb73170f2cd74f1ba1b5a909d90a0395
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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