Citric Acid → HCID 67125559, compound

HRID 1184924Notes

Reaction equation

HRID 1184924 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([NH:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:17]([OH:19])=O)=[O:12].[NH2:24][C:25]1[CH:26]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:29][CH:30]=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>CN1C(=O)CCC1>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([NH:13][C:14]1[CH:15]=[C:16]([C:17](=[O:19])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:26]=2)[CH:20]=[CH:21][C:22]=1[CH3:23])=[O:12]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 73753-(Trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67125637HCID 67125637, compound

Product 1

HCID 67125559HCID 67125559, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 109 (0.305 mmol, 100 mg), 3-aminobenzotrifluoride (0.305 mmol, 0.038 mL), TBTU (0.457 mmol, 147 mg) and DIPEA (0.914 mmol, 0.150 mL) in NMP (5 ml) stirred overnight at 80° C. The light brown solution was poured into citric acid solution and extracted with ethyl acetate. The combined organic layers were washed with brine and evaporated. The crude compound was purified by HPLC and chromatography (0-5% methanol in CH2Cl2) gave 7-amino-N-(2-methyl-5-(3-(trifluoromethyl)phenylcarbamoyl)phenyl)thieno[2,3-b]pyrazine-6-carboxamide 110 (14 mg, 10%). NMR (400 MHz, DMSO-d6) 2.33 (s, 3H), 7.10 (s, 2H), 7.47 (m, 2H), 7.61 (m, 1H), 7.85 (dd, J=7.8 Hz and 1.6 Hz, 1H), 8.00 (d, J=2.0 Hz, 1H), 8.09 (d, J=8.2 Hz, 1H), 8.25 (s, 1H), 8.79 (d, J=2.3 Hz, 1H), 8.80 (d, J=2.3 Hz, 1H), 9.62 (s, 1H), 10.52 (s, 1H). (m/z)=472 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customevaporated
  4. customThe crude compound was purified by HPLC and chromatography (0-5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-0435e821ca0642d386a0ee1bfa837e7e
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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