3,3,3-Trifluoropropylamine → N-(3,3,3-Trifluoro-propyl)-2-chloro-4-methylamino-5-nitro-benzoic acid amide

HRID 1189662Notes

Reaction equation

HRID 1189662 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][CH3:12])[C:8]([N+:13]([O-:15])=[O:14])=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:16][C:17]([F:22])([F:21])[CH2:18][CH2:19][NH2:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[F:16][C:17]([F:22])([F:21])[CH2:18][CH2:19][NH:20][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:13]([O-:15])=[O:14])[C:9]([NH:11][CH3:12])=[CH:10][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 100013,3,3-TrifluoropropylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 679575072-Chloro-4-(methylamino)-5-nitrobenzoic acid

Product 1

HCID 67957674N-(3,3,3-Trifluoro-propyl)-2-chloro-4-methylamino-5-nitro-benzoic acid amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The sub-title compound is prepared in analogy to 5c from 2-chloro-4-methylamino-5-nitro-benzoic acid (900 mg, 3.9 mmol), 3,3,3-trifluoro-propylamine (0.58 g, 3.9 mmol), TBTU (1.38 g, 4.2 mmol), DIPEA (2.0 mL, 11.7 mmol) and THF (20 mL).

Sources & evidence

ORD record
ord-970837954e2b48e8964c1171e5ab8358
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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