Toluene → HCID 69361977, compound

HRID 395854Notes

Reaction equation

HRID 395854 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[C:19](Cl)(Cl)=[O:20].C([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C.N1C=CC([N:36]2[CH2:41][CH2:40][CH:39]([CH2:42][OH:43])[CH2:38][CH2:37]2)=CC=1.[C:44]1(C)C=CC=CC=1>>[C:12]([O:11][C:9]([NH:8][C:6]1[CH:5]=[CH:4][C:3]([N+:16]([O-:18])=[O:17])=[C:2]([NH:1][C:19]([O:43][CH:42]([CH:44]2[CH2:27][CH2:26][NH:25][CH2:28][CH2:29]2)[C:39]2[CH:38]=[CH:37][N:36]=[CH:41][CH:40]=2)=[O:20])[CH:7]=1)=[O:10])([CH3:14])([CH3:15])[CH3:13]

Participants

6

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 11310048(1-(Pyridin-4-YL)piperidin-4-YL)methanolHCID 18174493HCID 18174493, compound

Product 1

HCID 69361977HCID 69361977, compoundYield 46%

Conditions

Temperature
50 °C

Procedure

A solution of 2-amino-4-(N-tert-butoxycarbonylamino)nitrobenzene (2.1 g, 8.3 mmol) in toluene (50 mL) was treated with phosgene (1.93M in toluene, 12.9 mL, 24.9 mmol) and the mixture-was heated at 50° C. After 2 h, the mixture was concentrated, the residue was dissolved in CH2Cl2 and treated with triethylamine (2.31 mL, 16.6 mmol) and 1-(4-pyridyl)piperidine-4-methanol (1.59 g, 8.29 mmol). After 16 h, the mixture was concentrated and the residue purified by chromatography (9:1 CH2Cl2:MeOH) affording 1.78 g (46%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. waitAfter 16 h
  4. concentrationthe mixture was concentrated
  5. customthe residue purified by chromatography (9:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-9992e4021935476589c824721a65978e
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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