Hydrochloric Acid → HCID 11856056, compound

HRID 1696512Notes

Reaction equation

HRID 1696512 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])=[O:12])[N:7]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27](C(OC(C)(C)C)=O)[N:26]=[CH:25]3)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.CCO.Cl>>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])=[O:12])[N:7]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][N:26]=[CH:25]3)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 21887872Ethanol hydrochlorideHCID 67271075HCID 67271075, compound

Product 1

HCID 11856056HCID 11856056, compoundYield 58.8%

Conditions

Temperature
80 °C

Procedure

t-Butyl 5-(3-t-butyl-5-(3-(2,3-dichlorophenyl)ureido)-1H-pyrazol-1-yl)-1H-indazole-1-carboxylate (0.1155 g, 0.213 mmol, 1.00 eq) was dissolved in satd. HCl/EtOH. The solution was heated at 80° C. for 1 h. After cooling to RT, the reaction was concentrated to dryness and treated with 80:20 MeCN/H2O. The resulting suspension was thoroughly chilled. The solids were collected by filtration, rinsed with 80:20 MeCN/H2O, MeCN and dried on the filter to yield 1-(3-t-butyl-1-(1H-indazol-5-yl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea (55.5 mg, 54.4% yield) as the HCl salt. 1H NMR (DMSO-d6): 9.18 (s, 1H), 8.76 (s, 1H), 8.19 (s, 1H), 8.08-8.06 (m, 1H), 7.89-7.88 (m, 1H), 7.70-7.67 (m, 1H), 7.47-7.44 (m, 1H), 7.33-7.28 (m, 2H), 6.40 (s, 1H), 1.29 (s, 9H); MS (ESI) m/z: 502.0 (M+H+), 504.0 (M+2+H+).

Workup

  1. temperatureAfter cooling to RT
  2. concentrationthe reaction was concentrated to dryness
  3. additiontreated with 80:20 MeCN/H2O
  4. temperatureThe resulting suspension was thoroughly chilled
  5. filtrationThe solids were collected by filtration
  6. washrinsed with 80:20 MeCN/H2O, MeCN
  7. customdried on the
  8. filtrationfilter

Sources & evidence

ORD record
ord-ef54190f764142079918ffb66e1e4695
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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