Citric Acid → 3-(2-cyanopropan-2-yl)-N-(2,4-difluoro-5-nitrophenyl)benzamide

HRID 1184882Notes

Reaction equation

[NH2:1][C:2]1C2C(=NC=CN=2)SC=1C(O)=O.[CH3:14]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN([CH:44]([CH3:46])[CH3:45])C(C)C.[F:47][C:48]1[CH:54]=[C:53]([F:55])[C:52]([N+:56]([O-:58])=[O:57])=[CH:51][C:49]=1[NH2:50].[C:59](O)(=O)[CH2:60][C:61]([CH2:66][C:67](O)=O)([C:63]([OH:65])=O)O>CN(C=O)C>[C:2]([C:44]([C:67]1[CH:66]=[C:61]([CH:60]=[CH:59][CH:14]=1)[C:63]([NH:50][C:49]1[CH:51]=[C:52]([N+:56]([O-:58])=[O:57])[C:53]([F:55])=[CH:54][C:48]=1[F:47])=[O:65])([CH3:45])[CH3:46])#[N:1]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 7-aminothieno[2,3-b]pyrazine-6-carboxylic acid 8 (179 mg, 0.948 mmol), HATU and DIPEA (0.313 mL, 1.895 mmol) in DMF (6 mL) was stirred at rt for 15 min. 2,4-difluoro-5-nitroaniline 71 (165 mg, 0.948 mmol) was added and stirred overnight at 60° C. Citric acid solution (3%) was added and extracted with EtOAc. Organic layer was washed twice water, brine, dried and evaporated. Purification by chromatography (20% EtOAc in heptane) gave 3-(2-cyanopropan-2-yl)-N-(2,4-difluoro-5-nitrophenyl)benzamide 72 (157 mg, 48%). (m/z)=346 (M+H)+.

Workup

extractionextracted with EtOAc
washOrganic layer was washed twice water, brine
customdried
customevaporated
customPurification by chromatography (20% EtOAc in heptane)

Sources & evidence

ORD record: ord-beb35513b3834930b618bf8105fd54c5
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669256B2

Reaction notes

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