3-(Trifluoromethyl)aniline → HCID 66552475, compound

HRID 1615873Notes

Reaction equation

HRID 1615873 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=O)[N:5]=2.C(N(CC)C(C)C)(C)C.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.[F:62][C:63]([F:72])([F:71])[C:64]1[CH:65]=[C:66]([CH:68]=[CH:69][CH:70]=1)[NH2:67].[NH4+].[Cl-]>CN(C=O)C>[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([NH:67][C:66]1[CH:68]=[CH:69][CH:70]=[C:64]([C:63]([F:62])([F:71])[F:72])[CH:65]=1)=[O:16])[N:5]=2

Participants

7

Reactant 5

HCID 73753-(Trifluoromethyl)anilineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 66552472HCID 66552472, compoundHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium

Product 1

HCID 66552475HCID 66552475, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution 3-(2-aminothiazolo[5,4-b]pyridin-5-yl)benzoic acid (310 mg, 1.14 mmol) in DMF (5.0 mL) was added N,N-diisopropylethylamine (0.56 mL, 3.42 mmol), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (649 mg, 1.71 mmol) and 3-(trifluoromethyl) aniline (0.28 mL, 2.28 mmol). The reaction mixture was stirred at room temperature for 16 h. The crude product was diluted with satd. NH4Cl solution (10 mL). The resulting brown solid was collected and washed with water and dried to give 320 mg (67% yield) of the 3-(2-aminothiazolo[5,4-b]pyridin-5-yl)-N-(3-(trifluoromethyl)phenyl)benzamide.

Workup

  1. customThe resulting brown solid was collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-b84df58dd4d74f5d9fdbeb333632859d
Source dataset
uspto-grants-2014_07
Patent number
US08765747B2

Reaction notes

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