Potassium Hydroxide → HCID 53329886, compound

HRID 1029040Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]#[N:9])[CH2:3][CH2:2]1.[OH-].[K+].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=2[N:26]([CH3:34])[C:27](=[O:33])[CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:15][C:14]=1[CH:35]=O>CS(C)=O.O.[Cl-].[NH4+]>[NH2:9][C:8]1[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:35][C:14]2[C:13](=[CH:18][CH:17]=[C:16]([C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=3[N:26]([CH3:34])[C:27](=[O:33])[CH2:28][C:29]([CH3:30])([CH3:32])[CH3:31])[CH:15]=2)[N:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-morpholinoacetonitrile (37.7 mg, 0.299 mmol) in DMSO (0.5 mL) was treated with concentrated aqueous KOH (11M; 8.08 μL, 0.095 mmol). The reaction mixture was heated to 80° C. and a solution of N-(4′-amino-3′-formyl-6-methylbiphenyl-2-yl)-N,3,3-trimethylbutanamide (64 mg, 0.189 mmol) in DMSO (1 mL) was added dropwise. After 10 min the reaction mixture was diluted with water and aqueous saturated ammonium chloride solution. The aqueous mixture was extracted with DCM. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by preparative HPLC (10-100% water with 0.1% TFA/CH3CN, 11 min). The titled compound was isolated as a light-yellow foam. MS (ESI, pos. ion) m/z: 447 (M+1).

Workup

extractionThe aqueous mixture was extracted with DCM
customThe organic phase was separated
dry with materialdried over MgSO4
customThe solvent was removed under reduced pressure
customthe remaining residue was purified by preparative HPLC (10-100% water with 0.1% TFA/CH3CN, 11 min)

Sources & evidence

ORD record: ord-87e90af8906d43dc80c0481480b91956
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735384B2

Reaction notes

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