HCID 131736985, compound → HCID 131736986, compound

HRID 58203Notes

Reaction equation

HRID 58203 reaction equation
[C:1]([O:5][C:6]([N:8]([C:31]1[CH:36]=[C:35]([N:37]([CH3:61])[C:38]([N:40]([C:49]2[C:54]([Cl:55])=[C:53]([O:56][CH3:57])[CH:52]=[C:51]([O:58][CH3:59])[C:50]=2[Cl:60])[CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])=[O:39])[N:34]=[CH:33][N:32]=1)[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[CH:11][C:10]=1[N+:28]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.CO.[Ni].O>[NH2:28][C:10]1[CH:11]=[C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH:13]=[CH:14][C:9]=1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:31]1[CH:36]=[C:35]([N:37]([CH3:61])[C:38]([N:40]([C:49]2[C:50]([Cl:60])=[C:51]([O:58][CH3:59])[CH:52]=[C:53]([O:56][CH3:57])[C:54]=2[Cl:55])[CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:46])[CH3:47])=[O:39])[N:34]=[CH:33][N:32]=1

Participants

6

Reactant 1

HCID 131736985HCID 131736985, compound

Product 1

HCID 131736986HCID 131736986, compound

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-butyl 4-(4-((tert-butoxycarbonyl)(6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)ureido)pyrimidin-4-yl)amino)-3-nitrophenyl)piperazine-1-carboxylate (149 g, 0.164 mmol) was stirred in THF (1.5 ml) and MeOH (1.5 ml). Five drops of Raney Nickel suspension in water was added. The solution was stirred under hydrogen atmosphere at room temperature overnight. The reaction was filtered through a pad of Celite®. and filtrate was concentrated to give crude title compound which was taken to the next step without further purification. ESI-MS: 877 [M+H]+.

Workup

  1. filtrationThe reaction was filtered through a pad of Celite®
  2. concentrationand filtrate was concentrated

Sources & evidence

ORD record
ord-cf6879ebef9b450da44b811eacffcf0e
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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