Water → Carbamic acid, N-(2-((((1-methyl-5-((triphenylmethyl)amino)-1H-pyrazol-4-yl)amino)carbonyl)amino)ethyl)-, 1,1-dimethylethyl ester

HRID 1247805Notes

Reaction equation

HRID 1247805 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH:27][C:28](OC2C=CC=CC=2)=[O:29])[CH:4]=[N:3]1.C(N(CC)CC)C.[NH2:44][CH2:45][CH2:46][NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51].O>CN(C)C=O>[C:50]([O:49][C:48]([NH:47][CH2:46][CH2:45][NH:44][C:28]([NH:27][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[NH:7][C:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:29])=[O:54])([CH3:53])([CH3:52])[CH3:51]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 21904567Phenyl [1-methyl-5-(tritylamino)pyrazol-4-yl]carbamate

Product 1

HCID 21904455Carbamic acid, N-(2-((((1-methyl-5-((triphenylmethyl)amino)-1H-pyrazol-4-yl)amino)carbonyl)amino)ethyl)-, 1,1-dimethylethyl esterYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 1-methyl-4-phenoxycarbonylamino-5-triphenylmethylaminopyrazole (253.6 g) in N,N-dimethylformamide (1.5 L) were added triethylamine (59.5 g) and tert-butyl N-(2-aminoethyl)carbamate (94.2 g) in N,N-dimethylformamide (254 ml). The mixture was stirred for 5 hours and poured into water (10.6 L). The slurry was stirred for 1 hour. The precipitated solid was collected by filtration and dried to give a crude product. The crude product was suspended in N,N-dimethylformamide, and the suspension was heated under reflux for 20 minutes. The suspension was cooled to ambient temperature over 4 hours. The solid was collected by filtration, washed with acetonitrile and dried to give 4-[N-(2-tert-butoxycarbonylaminoethyl)carbamoylamino]-1-methyl-5-triphenylmethylaminopyrazole (261.2 g).

Workup

  1. stirringThe slurry was stirred for 1 hour
  2. filtrationThe precipitated solid was collected by filtration
  3. customdried
  4. customto give a crude product
  5. temperaturethe suspension was heated
  6. temperatureunder reflux for 20 minutes
  7. filtrationThe solid was collected by filtration
  8. washwashed with acetonitrile
  9. customdried

Sources & evidence

ORD record
ord-e6ae05436d334f328b0fb447fd5bfe52
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

Loading…