Ammonia → HCID 20789025, compound

HRID 1349595Notes

Reaction equation

HRID 1349595 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:31])[NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18](C(=O)C)[N:17]=[C:16]2[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=O)C.N.Cl>CO>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[C:16]2[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:31]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 22479775HCID 22479775, compound

Product 1

HCID 20789025HCID 20789025, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[N-(1-acetyl-3-phenyl-1H-indazole-5-yl)carbamoyl]phenyl acetate (100 mg, 0.241 mmol) in methanol (11 mL) with 0.3% ammonia was allowed to stir for three hours at reflux temperature. The mixture was then acidified with 5% HCl solution until neutral pH. The resulting solid was filtered, dried and triturated with hexanes to give the title compound (45 mg, 57% yield). 1H NMR (DMSO-d6) δ 13.23 (br s, 1H), 11.92 (br s, 1H), 10.47 (s, 1H), 8.45 (s, 1H), 7.96 (m, 3H), 7.51 (m, 6H), 6.95 (d, 2H); ES-MS (m/z) 330 [M+1]+.

Workup

  1. temperatureat reflux temperature
  2. filtrationThe resulting solid was filtered
  3. customdried
  4. customtriturated with hexanes

Sources & evidence

ORD record
ord-37d80cbdf2db4768b8b54c1cb0e38471
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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