Thionyl Chloride → HCID 178482120, compound

HRID 341498Notes

Reaction equation

HRID 341498 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[N:18]=[C:17]([N:19]([CH3:26])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:16]=[C:15]([NH2:27])[N:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH:28]C1N=CC(C(O)=O)=CC=1.S(Cl)(Cl)=O.NC1N=C(N(C)C2C=CC=CC=2)N=C(C(=N)NO)N=1.NC1N=C(N(C)C2C=CC=C(C)C=2)N=C(C(NO)=N)N=1>>[NH2:27][C:15]1[N:16]=[C:17]([N:19]([CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:18]=[C:13]([C:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:28])=[N:7][CH:6]=3)[O:12][N:11]=2)[N:14]=1

Participants

6

Reactant 5

HCID 24386Thionyl ChlorideHCID 867105136-[5-(6-chloropyridin-3-yl)-1,2,4-oxadiazol-3-yl]-2-N-methyl-2-N-phenyl-1,3,5-triazine-2,4-diamineHCID 178418479HCID 178418479, compoundHCID 1784255374-amino-N-hydroxy-6-(methyl-3-methylphenyl-amino)-[1,3,5]triazine-2-carboxamidineHCID 1784821214-Amino-N-hydroxy-6-[methyl(phenyl)amino]-1,3,5-triazine-2-carboximidamide

Product 1

HCID 178482120HCID 178482120, compound

Procedure

Prepared according to the method described for Intermediate 135 above from 6-Hydroxypyridine-3-carboxylic acid (0.556 g, 4 mmol, thionyl chloride (1.2 mL, 16 mmol) and 4-amino-N-hydroxy-6-[methyl(phenyl)amino]-1,3,5-triazine-2-carboximidamide (prepared in an analogous manner to Intermediate 1, 0.52 g, 2 mmol). Method B HPLC-MS: MH+ requires m/z=363 Found: m/z=363, Rt=1.52 min (87%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3d79f2faef114778932e04265dd3bb7d
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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