Hydrochloric Acid → HCID 58851425, compound

HRID 1696507Notes

Reaction equation

HRID 1696507 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:30]=[C:29]3[C:25]([CH:26]=[N:27][N:28]3C(OC(C)(C)C)=O)=[CH:24][CH:23]=2)[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:30]=[C:29]3[C:25]([CH:26]=[N:27][NH:28]3)=[CH:24][CH:23]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 21887872Ethanol hydrochlorideHCID 67272134HCID 67272134, compound

Product 1

HCID 58851425HCID 58851425, compoundYield 91.6%

Procedure

A solution of yield of t-butyl 6-(3-t-butyl-5-(3-(2,3-dichlorophenyl)ureido)-1H-pyrazol-1-yl)-1H-indazole-1-carboxylate (0.13 g, 0.239 mmol, 1.00 eq) in satd. HCl/EtOH (5.00 ml) and stirred at 65° C. for 2 h until the reaction was clear and homogeneous. It was cooled to RT and evaporated. The syrupy residue was dissolved in MeCN/H2O, frozen and lyophilized to yield 1-(3-t-butyl-1-(1H-indazol-6-yl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea (97.1 mg, 85% yield) as the HCl salt. 1H NMR (DMSO-d6): δ 9.32 (s, 1H), 8.81 (s, 1H), 8.17-8.16 (m, 1H), 8.13-8.12 (m, 1H), 8.10-8.07 (m, 1H), 7.92-7.82 (m, 1H), 7.65-7.59 (m, 1H), 7.24-7.25 (m, 2H), 6.44 (s, 1H), 1.30 (s, 9H); MS (ESI) m/z: 443.0 (M+H+), 445.0 (M+2+H+).

Workup

  1. customevaporated
  2. dissolutionThe syrupy residue was dissolved in MeCN/H2O
  3. temperaturefrozen

Sources & evidence

ORD record
ord-e44421ba77aa4345818b87530f05c549
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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