Methanol → HCID 11706027, compound

HRID 1696588Notes

Reaction equation

HRID 1696588 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:32])[NH:11][C:12]1[N:16]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[CH:19][CH:18]=2)[N:15]=[C:14]([C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[CH:13]=1.[CH2:33]1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CO.O>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:32])[NH:11][C:12]1[N:16]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][C:24]([O:26][CH3:33])=[O:25])=[CH:21][CH:22]=2)[N:15]=[C:14]([C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[CH:13]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2724699PyBOPHCID 11540374HCID 11540374, compound

Product 1

HCID 11706027HCID 11706027, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(5-(3-(2,3-dichlorophenyl)ureido)-3-(thiophen-3-yl)-1H-pyrazol-1-yl)phenyl)acetic acid (0.073 g, 0.15 mmol) in DMF (1 ml) were added PyBop (0.18 mmol) and MeOH (0.1 g, 0.45 mmol) and stirred for 4 h at RT. The reaction mixture was poured into cold H2O and the product was extracted with EtOAc (3×20 ml). The combined organic extracts were washed with 3M HCl, brine, dried (Na2SO4) and concentrated to yield a crude product. To the crude product was added CH2Cl2 (2 ml) and stirred for 10 min and the resultant solid was filtered and dried to afford pure methyl 2-(4-(5-(3-(2,3-dichlorophenyl)ureido)-3-(thiophen-3-yl)-1H-pyrazol-1-yl)phenyl)acetate. 1H NMR (400 MHz, DMSO-d6): δ 9.40 (s, 1H), 8.87 (s, 1H), 8.10 (dd, J=6.8 Hz, 2.4 Hz, 1H), 7.87-7.86 (m, 1H), 7.60 (dd, J=4.8 Hz, 2.8 Hz, 1H), 7.57 (d, J=8.0 Hz, 2H), 7.52-7.49 (m, 1H), 7.48 (d, J=8.0 Hz, 2H), 7.34-7.32 (m, 2H), 6.85 (s, 1H), 3.80 (s, 2H), 3.65 (s, 3H); MS (ESI) m/z: 501.0 (M+H+).

Workup

  1. extractionthe product was extracted with EtOAc (3×20 ml)
  2. washThe combined organic extracts were washed with 3M HCl, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto yield a crude product
  6. stirringstirred for 10 min
  7. filtrationthe resultant solid was filtered
  8. customdried

Sources & evidence

ORD record
ord-b9491d77d30045b7b422101de9ffdde4
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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