tert-Butanol → HCID 86592856, compound

HRID 351243Notes

Reaction equation

HRID 351243 reaction equation
[NH2:1][C:2]([NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[N:17]=[C:16](C(O)=O)[CH:15]=2)=[CH:10][CH:9]=1)=[O:3].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])C=CC=CC=1.CC[N:49]([CH2:52]C)CC.[C:54]([OH:58])([CH3:57])([CH3:56])[CH3:55]>>[NH2:1][C:2]([NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:18]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[N:17]=[C:16]([NH:49][C:52](=[O:37])[O:58][C:54]([CH3:57])([CH3:56])[CH3:55])[CH:15]=2)=[CH:12][CH:13]=1)=[O:3]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 21090965HCID 21090965, compound

Product 1

HCID 86592856HCID 86592856, compound

Procedure

A mixture of 5-(4-{2-[(aminocarbonyl)amino]ethoxy}-phenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid (1.56 g), diphenylphosphoryl azide (1.62 g), and Et3N (597 mg) in t-butanol (5 ml) was refluxed for 3 hours. The mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate and H2O. The combined organic layer was washed twice with 1M HC1. and washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography elutedwith ethyl acetate to give tert-butyl [5-(4-{2-[(aminocarbonyl)amino]-ethoxy}phenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]carbamate (519 mg) as an amorphous powder.

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and H2O
  4. washThe combined organic layer was washed twice with 1M HC1
  5. washand washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography elutedwith ethyl acetate

Sources & evidence

ORD record
ord-7825804f4cb6461b8fcb6f6c686c59a2
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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