4-Aminobenzonitrile → HCID 60773727, compound

HRID 2235128Notes

Reaction equation

N1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]3[CH:23]=[C:22]4[C:18]([CH2:19][CH2:20][N:21]4S(C4C=C(Cl)C=CC=4OC)(=O)=O)=[CH:17][CH:16]=3)=[O:14])=[CH:8][CH:7]=2)=[N:4]N=N1.NC1C=CC(C#N)=CC=1>>[C:5]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]([C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[CH:20][NH:21]3)=[CH:17][CH:16]=2)=[O:14])=[CH:10][CH:11]=1)#[N:4]

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 178490719HCID 178490719, compound

Product 1

HCID 60773727HCID 60773727, compound

Procedure

1-(5-Chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(1H-tetrazol-5-yl)-phenyl]-amide, MS (ISP), m/e=509.1 (M−H), was prepared in analogy to example 13, steps 1 to 4. Step 1 was performed using 4-amino-benzonitrile and yielded 1H-indole-6-carboxylic acid (4-cyano-phenyl)-amide which was reduced to 2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-phenyl)-amide in step 2. This was coupled with 5-chloro-2-methoxy benzenesulfonyl chloride in step 3, yielding 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-phenyl)-amide, which was converted to 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(1H-tetrazol-5-yl)-phenyl]-amide by reaction with ammonium azide in step 4.

Sources & evidence

ORD record: ord-25a5771366c94a29954e8b54fc71d663
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713996B2

Reaction notes

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