Dimethylformamide → HCID 59459117, compound

HRID 1874261Notes

Reaction equation

[NH2:1][CH:2]([C:7]([F:10])([F:9])[F:8])[CH2:3][C:4](O)=[O:5].[C:11]1(=O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[O:12]1.C[N:23](C=O)C>>[O:12]=[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[N:1]1[CH:2]([C:7]([F:10])([F:9])[F:8])[CH2:3][C:4]([NH2:23])=[O:5]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 6811Phthalic Anhydride

HCID 3429703-Amino-4,4,4-trifluorobutanoic acid

Product 1

HCID 59459117HCID 59459117, compoundYield 54%

Procedure

A solution of 3-amino-4,4,4-trifluorobutanoic acid (628 mg, 4 mmol) and isobenzofuran-1,3-dione (592 mg, 4 mmol) in DMF (5 mL) was heated to 140° C. under microwave irradiation for 15 min. The reaction mixture was purified by preparative HPLC (Axia luna column, 30×75 mm, 10-100% ACN/H2O with 0.1% TFA over 10 min, flow rate 40 mL/min, monitoring at 220 nm) to yield 3-(1,3-dioxoisoindolin-2-yl)-4,4,4-trifluorobutanamide (620 mg, 54% yield). LCMS: RT=1.54 min [M+H] 288.2 (Phenomenex Luna C18 column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm).

Workup

customThe reaction mixture was purified by preparative HPLC (Axia luna column, 30×75 mm, 10-100% ACN/H2O with 0.1% TFA over 10 min, flow rate 40 mL/min, monitoring at 220 nm)

Sources & evidence

ORD record: ord-0ecf8d349af94d26a8e2159855a1923b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304403B2

Reaction notes

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