Citric Acid → HCID 67125676, compound

HRID 1184863Notes

Reaction equation

HRID 1184863 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[NH:11][C:12]([C:14]1[S:22][C:17]2=[N:18][CH:19]=[CH:20][N:21]=[C:16]2[CH:15]=1)=[O:13].[NH2:23][C:24]1[CH:25]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:28][CH:29]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:8])[NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=2)=[CH:4][C:3]=1[NH:11][C:12]([C:14]1[S:22][C:17]2=[N:18][CH:19]=[CH:20][N:21]=[C:16]2[CH:15]=1)=[O:13]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 73753-(Trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67125632HCID 67125632, compound

Product 1

HCID 67125676HCID 67125676, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-methyl-3-(thieno[2,3-b]pyrazine-6-carboxamido)benzoic acid 50 (25 mg, 0.080 mmol), 3-aminobenzotrifluoride (9.87 μl, 12.86 mg, 0.080 mmol), TBTU (38.4 mg, 0.120 mmol) and DIPEA (0.039 mL, 0.239 mmol) in DMF (1 mL) under a nitrogen atmosphere was stirred overnight at 40° C. The reaction mixture was poured into 3% citric acid solution. The resulting precipitation was collected and washed with water to give the title compound N-(2-methyl-5-(3-(trifluoromethyl)phenylcarbamoyl)phenyl)thieno[2,3-b]pyrazine-6-carboxamide 51 (19 mg, 53%). NMR (400 MHz, DMSO-d6) 2.38 (s, 3H), 7.46 (d, J=7.4 Hz, 1H), 7.53 (d, J=8.2 Hz, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.90 (dd, J=7.8 and 1.6 Hz, 1H), 8.04 (d, J=1.6 Hz, 1H), 8.09 (d, J=8.6 Hz, 1H), 8.25 (s, 1H), 8.57 (s, 1H), 8.77 (d, J=2.3 Hz, 1H), 8.90 (d, J=2.3 Hz, 1H), 10.55 (s, 1H), 10.66 (s, 1H). (m/z)=457 (M+H)+.

Workup

  1. customThe resulting precipitation
  2. customwas collected
  3. washwashed with water

Sources & evidence

ORD record
ord-14be80f1ac064669a98ba771f5d8d123
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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