2-[2-(tert-butyldimethylsilanyloxy)propyl]-4,6,7-trichloro-2H-indazole → 2-Amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrile

HRID 415779Notes

Reaction equation

HRID 415779 reaction equation
[Cl:1][C:2]1[C:3]2[C:7]([C:8]([Cl:12])=[C:9]([Cl:11])[CH:10]=1)=[N:6][N:5]([CH2:13][C:14](=O)[CH3:15])[CH:4]=2.[Si](OC(C)[CH2:26][N:27]1C=C2C(C(Cl)=C(Cl)C=C2Cl)=N1)(C(C)(C)C)(C)C.[Si:40]([O:47][CH:48]([CH3:64])[CH2:49][NH:50][CH2:51][C:52]1[C:57]([Cl:58])=[CH:56][C:55]([Cl:59])=[C:54]([Cl:60])[C:53]=1[N+:61]([O-:63])=[O:62])([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41].[N+](C1C(Cl)=C(Cl)C=C(Cl)C=1C=O)([O-])=O>>[NH2:50][C:14]([CH3:15])([CH2:13][N:5]1[CH:4]=[C:3]2[C:7]([C:8]([Cl:12])=[C:9]([Cl:11])[CH:10]=[C:2]2[Cl:1])=[N:6]1)[C:26]#[N:27].[Cl:58][C:57]1[C:52]2[C:53]([C:54]([Cl:60])=[C:55]([Cl:59])[CH:56]=1)=[N:61][N:50]([CH2:49][C:48](=[O:47])[CH3:64])[CH:51]=2.[Si:40]([O:47][CH:48]([CH3:64])[CH2:49][NH:50][CH2:51][C:52]1[C:57]([Cl:58])=[CH:56][C:55]([Cl:59])=[C:54]([Cl:60])[C:53]=1[N+:61]([O-:63])=[O:62])([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]

Participants

7

Reactant 4

HCID 666201752-[2-(tert-butyldimethylsilanyloxy)propyl]-4,6,7-trichloro-2H-indazoleHCID 666207131-(4,6,7-Trichloro-2H-indazol-2-yl)propan-2-oneHCID 86625589[2-(tert-Butyldimethylsilanyloxy)propyl]-(2-nitro-3,4,6-trichlorobenzyl)amineHCID 866255902-Nitro-3,4,6-trichlorobenzaldehyde

Product 3

HCID 666207131-(4,6,7-Trichloro-2H-indazol-2-yl)propan-2-oneHCID 666208912-Amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrileYield 60%HCID 86625589[2-(tert-Butyldimethylsilanyloxy)propyl]-(2-nitro-3,4,6-trichlorobenzyl)amineYield 44%

Procedure

2-Amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrile (0.16 g, 60%) was prepared using a procedure similar to that described in Example 1, part b, except starting from 1-(4,6,7-trichloro-2H-indazol-2-yl)propan-2-one (0.25 g). 1-(4,6,7-Trichloro-2H-indazol-2-yl)propan-2-one was prepared using a procedure similar to that described in Example 105 part c and d except starting from 2-[2-(tert-butyldimethylsilanyloxy)propyl]-4,6,7-trichloro-2H-indazole (1.4 g, 69%) that was prepared using a procedure similar to that described in Example 132 part a except starting from [2-(tert-butyldimethylsilanyloxy)propyl]-(2-nitro-3,4,6-trichlorobenzyl)amine (2.2 g). [2-(tert-Butyldimethylsilanyloxy)propyl]-(2-nitro-3,4,6-trichlorobenzyl)amine (2.2 g, 44%) was prepared using a procedure similar to that described in Example 105 part a except starting from 2-nitro-3,4,6-trichlorobenzaldehyde (3 g) that was prepared as follows:

Workup

  1. customwas prepared
  2. customwas prepared

Sources & evidence

ORD record
ord-ccfb3ef21c424fef9abb842404c7c28c
Source dataset
uspto-grants-2012_01
Patent number
US08088801B2

Reaction notes

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