2-Methoxybenzoic acid → HCID 67070999, compound

HRID 732067Notes

Reaction equation

HRID 732067 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[CH3:35][O:36][C:37]1[CH:45]=[CH:44][CH:43]=[CH:42][C:38]=1[C:39]([OH:41])=O.CCN(C(C)C)C(C)C.O[NH:56][C:57](=[NH:71])[CH2:58][S:59][C:60]1[N:64]([CH3:65])[C:63]([C:66]2[S:67][CH:68]=[CH:69][CH:70]=2)=[N:62][N:61]=1>CN(C=O)C.O>[CH3:35][O:36][C:37]1[CH:45]=[CH:44][CH:43]=[CH:42][C:38]=1[C:39]1[O:41][N:71]=[C:57]([CH2:58][S:59][C:60]2[N:64]([CH3:65])[C:63]([C:66]3[S:67][CH:68]=[CH:69][CH:70]=3)=[N:62][N:61]=2)[N:56]=1

Participants

8

Reactant 5

HCID 113702-Methoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178481652HCID 178481652, compound

Product 1

HCID 67070999HCID 67070999, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HBTU (171 mg, 0.45 mmol) and HOBT (8 mg, 0.06 mmol) were added to a solution of 2-methoxy benzoic acid (68 mg, 0.45 mmol) and DIPEA (192 ml, 1.11 mmol) in DMF (3 ml). After 10 min N-hydroxy-2-(4-methyl-5-thiophen-2-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-acetamidine (100 mg, 0.37 mmol) was added. The reaction mixture was stirred at RT for 7 h and then at 110° C. over night. After cooling the reaction mixture was diluted with water and extracted with CH2Cl2. The organic phase was dried and concentrated. Flash chromatography (heptane/EtOAc 1:2) afforded 1.9 mg (11%) of the desired product.

Workup

  1. waitat 110° C. over night
  2. temperatureAfter cooling the reaction mixture
  3. extractionextracted with CH2Cl2
  4. customThe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e99fdd04e93f40cea41fdf1b34e35fce
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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