Water → HCID 86597874, compound

HRID 459621Notes

Reaction equation

HRID 459621 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH:8]([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].N12CCCN=C1CCCCC2.[C:38](Cl)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.O>C(Cl)Cl>[CH3:7][N:6]1[C:2]([NH:1][C:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[C:3]([CH:8]([CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:16])[CH3:14])[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:4]=[N:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86597875HCID 86597875, compound

Product 1

HCID 86597874HCID 86597874, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of di-tert-butyl [2-(5-amino-1-methyl-1H-pyrazol-4-yl)-1,3-propanediyl]biscarbamate (1.27 g) in methylene chloride (10 ml) were added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.05 g) and trityl chloride (1.44 g) at room temperature. The mixture was stirred for 2 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to give di-tert-butyl {2-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]-1,3-propanediyl}biscarbamate (1.7 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-4c1d1399793a46c98ddef31ff775c230
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

Loading…