1-(2-Isocyanatoethyl)-3-methoxybenzene → Tert-butyl-3-amino-5-{3-[2-(3-methoxyphenyl)ethyl]ureido}indazole-1-carboxylate

HRID 222386Notes

Reaction equation

HRID 222386 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:3]=1.[N:19]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1)=[C:20]=[O:21]>ClCCl>[C:15]([O:14][C:12]([N:4]1[C:5]2[C:10](=[CH:9][C:8]([NH:11][C:20]([NH:19][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=3)=[O:21])=[CH:7][CH:6]=2)[C:2]([NH2:1])=[N:3]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 205726701-(2-Isocyanatoethyl)-3-methoxybenzeneHCID 23571038tert-butyl 3,5-diamino-1H-indazole-1-carboxylate

Product 1

HCID 68918447Tert-butyl-3-amino-5-{3-[2-(3-methoxyphenyl)ethyl]ureido}indazole-1-carboxylateYield 54.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.1 700 mg of tert-butyl 3,5-diaminoindazole-1-carboxylate (3.1 mmol) and 532 mg of 1-(2-isocyanatoethyl)-3-methoxybenzene (3.0 mmol) are stirred at RT for 24 hours in 10 ml of dichloromethane. The reaction mixture is washed with water, the organic phase is separated off, dried and evaporated. Purification of the residue by column chromatography (eluent:ethyl acetate) gives 700 mg of tert-butyl-3-amino-5-{3-[2-(3-methoxyphenyl)ethyl]ureido}indazole-1-carboxylate (53%), MS-FAB (M+H+)=426.

Workup

  1. washThe reaction mixture is washed with water
  2. customthe organic phase is separated off
  3. customdried
  4. customevaporated
  5. customPurification of the residue by column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-e3cd3f54caf54ec2927be46b82aa3a4f
Source dataset
uspto-grants-2012_06
Patent number
US08207210B2

Reaction notes

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