Lithium borohydride → HCID 89662848, compound

HRID 1479077Notes

Reaction equation

HRID 1479077 reaction equation
[BH4-].[Li+].C([O:5][C:6](=O)[C:7]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([N:19]1[CH2:33][C:22]2=[C:23]3[N:28]([N:29]=[C:21]2[CH2:20]1)[C:27]([CH3:30])=[C:26]([Cl:31])[C:25]([CH3:32])=[N:24]3)=[O:18])([F:9])[F:8])C>O1CCOCC1.CC(=O)OCC>[Cl:31][C:26]1[C:25]([CH3:32])=[N:24][C:23]2[N:28]([N:29]=[C:21]3[CH2:20][N:19]([C:17]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[O:10][C:7]([F:8])([F:9])[CH2:6][OH:5])=[O:18])[CH2:33][C:22]3=2)[C:27]=1[CH3:30]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 89650618HCID 89650618, compound

Product 1

HCID 89662848HCID 89662848, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Lithium borohydride (2.81 mg; 0.13 mmol; 1 eq.) was added to a solution of [2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxy]-difluoro-acetic acid ethyl ester (60 mg; 0.13 mmol; 1 eq.) in 1,4-dioxane (1 mL) and the resulting mixture was stirred at room temperature for 1.5 hour. The solution was diluted with EA, washed with brine, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (30% to 75% EA in cyclohexane) followed by crystallization from ACN afforded the title compound (12 mg, 22%). HPLC (max plot) 98.4%, Rt 3.46 min. UPLC/MS: (MS+) 423.2 ([M+H]+).

Workup

  1. washwashed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (30% to 75% EA in cyclohexane)
  5. customfollowed by crystallization from ACN

Sources & evidence

ORD record
ord-e89e850d5ed24733bd68a220da702f7a
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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