Diisopropylethylamine → 5-Amino-2-fluoro-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide

HRID 335319Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][NH2:15])[CH2:4][CH2:3]1.[NH2:16][C:17]1[C:18]([CH3:27])=[CH:19][C:20]([F:26])=[C:21]([CH:25]=1)[C:22](O)=[O:23].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:16][C:17]1[C:18]([CH3:27])=[CH:19][C:20]([F:26])=[C:21]([CH:25]=1)[C:22]([NH:15][CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)=[O:23]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture comprising (2-(4-methylpiperazin-1-yl)phenyl)methanamine (413 mg, 2.010 mmol) and 5-amino-2-fluoro-4-methylbenzoic acid (step 2) (340 mg, 2.010 mmol) in DMF (3 ml) was treated with DIPEA (0.351 ml, 2.010 mmol) followed by HATU (764 mg, 2.010 mmol) and stirred at 25° C. for 24 hrs. The mixture was partitioned between water and EtOAc. The organic portion was washed with sat. aq. NaHCO3, 0.5 M LiCl and brine (each back extracted with EtOAc). The combined organic layers were dried (MgSO4), filtered and evaporated to dryness to give a pink oil. Purification by chromatography on silica eluting with 0-20% MeOH in DCM afforded the title compound;

Workup

customThe mixture was partitioned between water and EtOAc
washThe organic portion was washed with sat. aq. NaHCO3, 0.5 M LiCl and brine (each back
extractionextracted with EtOAc)
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered
customevaporated to dryness
customto give a pink oil
customPurification by chromatography on silica eluting with 0-20% MeOH in DCM

Sources & evidence

ORD record: ord-1ae9bf6293c343478c2851864051ba76
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883819B2

Reaction notes

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