1-(4,6-Dichloro-2H-indazol-2-yl)propan-2-one → 2-Amino-3-(4,6-dichloro-2H-indazol-2-yl)-2-methylpropionitrile

HRID 415777Notes

Reaction equation

HRID 415777 reaction equation
[Cl:1][C:2]1[C:3]2[C:7]([CH:8]=[C:9]([Cl:11])[CH:10]=1)=[N:6][N:5]([CH2:12][C:13](=O)[CH3:14])[CH:4]=2.[Si](OC(C)[CH2:25][N:26]1C=C2C(C=C(Cl)C=C2Cl)=N1)(C(C)(C)C)(C)C.[Si]([O:45][CH:46]([CH3:61])[CH2:47][NH:48][CH2:49][C:50]1[C:55]([N+:56]([O-])=O)=[CH:54][C:53]([Cl:59])=[CH:52][C:51]=1[Cl:60])(C(C)(C)C)(C)C>>[NH2:48][C:13]([CH3:14])([CH2:12][N:5]1[CH:4]=[C:3]2[C:7]([CH:8]=[C:9]([Cl:11])[CH:10]=[C:2]2[Cl:1])=[N:6]1)[C:25]#[N:26].[Cl:60][C:51]1[C:50]2[C:55]([CH:54]=[C:53]([Cl:59])[CH:52]=1)=[N:56][N:48]([CH2:47][C:46](=[O:45])[CH3:61])[CH:49]=2

Participants

5

Reactant 3

HCID 666202011-(4,6-Dichloro-2H-indazol-2-yl)propan-2-oneHCID 66620204[2-(Tert-butyldimethylsilanyloxy)propyl]-(2,4-dichloro-6-nitrobenzyl)amineHCID 666211362-[2-(tert-butyldimethylsilanyloxy)propyl]-4,6-dichloro-2H-indazole

Product 2

HCID 666199752-Amino-3-(4,6-dichloro-2H-indazol-2-yl)-2-methylpropionitrileYield 54%HCID 666202011-(4,6-Dichloro-2H-indazol-2-yl)propan-2-one

Procedure

2-Amino-3-(4,6-dichloro-2H-indazol-2-yl)-2-methylpropionitrile (88 mg, 54%) was prepared using a procedure similar to that described in Example 1, part b, except starting from 1-(4,6-dichloro-2H-indazol-2-yl)propan-2-one (146 mg). 1-(4,6-Dichloro-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-dichloro-2H-indazole that was prepared using a procedure similar to that described in Example 132 part a except starting from [2-(tert-butyldimethylsilanyloxy)propyl]-(2,4-dichloro-6-nitrobenzyl)amine described in Example 116.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-9a8730bc53cc4c5ab3be1a11922ba7a0
Source dataset
uspto-grants-2012_01
Patent number
US08088801B2

Reaction notes

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