Triethylamine → N-(2-Amino-5-fluoro-phenyl)-5-bromo-2-chloro-benzamide

HRID 77072

Reaction equation

HRID 77072 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[F:12][C:13]1[CH:14]=[C:15]([NH2:20])[C:16]([NH2:19])=[CH:17][CH:18]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C>O.CN(C)C=O.ClCCl>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([F:12])=[CH:14][C:15]=1[NH:20][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[Cl:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 331275-Bromo-2-chlorobenzoic acidHCID 1645844-Fluorobenzene-1,2-diamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 63257336N-(2-Amino-5-fluoro-phenyl)-5-bromo-2-chloro-benzamideYield 69%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Method 3,4—Step a To a mixture of the solids 5-Bromo-2-chlorobenzoic acid (7.00 g, 29.79 mmol), 4-Fluoro-benzene-1,2-diamine (4.65 g, 36.94 mmol) and O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (11.89 g, 31.28 mmol), triethylamine (TEA) (4.60 mL, 32.77 mmol), dichloromethane (120 mL) and dimethylformamide (DMF) (30 mL) were added. The reaction mixture was stirred at room temperature overnight, water was added (30 mL) and stirred until the formation of a precipitate. The precipitate was filtered off, washed with dichloromethane (3×10 mL) and dried to afford 6.90 g of the title compound (69%).

Workup

  1. additionwere added
  2. stirringstirred until the formation of a precipitate
  3. filtrationThe precipitate was filtered off
  4. washwashed with dichloromethane (3×10 mL)
  5. customdried

Sources & evidence

ORD record
ord-b8fafa47562a4f1b80cb580c176203c0
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Linked notes

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