Hydrochloric Acid → HCID 22135723, compound

HRID 1827209Notes

Reaction equation

HRID 1827209 reaction equation
[N+:1]([C:4]1[C:5]([NH2:29])=[N:6][C:7]([NH:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([S:18]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:20])=[O:19])[CH2:14][CH2:13]2)=[CH:8][CH:9]=1)([O-])=O.[H][H].N[C:33]1C=CN=C(N)C=1N.Cl.[OH-].[Na+]>C1COCC1.CO.[Ni].C(O)=O>[NH:1]1[C:4]2[C:5](=[N:6][C:7]([NH:10][CH2:11][CH:12]3[CH2:17][CH2:16][N:15]([S:18]([CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)(=[O:20])=[O:19])[CH2:14][CH2:13]3)=[CH:8][CH:9]=2)[N:29]=[CH:33]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22135565Pyridine-2,3,4-triamineHCID 23577247HCID 23577247, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22135723HCID 22135723, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 284Formic AcidSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

EXAMPLE 104 was prepared from 3-nitro-N6-[1-(2-phenyl-ethanesulfonyl)-piperidin-4-ylmethyl]-pyridine-2,6-diamine (EXAMPLE 103) (1 mmol scale) by hydrogenation in 15 mL of THF/methanol over 0.5 of Raney-nickel under 1 atm of hydrogen for 1 h, followed by immediate conversion of the crude, air sensitive triaminopyridine into the imidazo[4,5b]pyridine by heating with 5 mL of 96% formic acid and 2 mL of 37% hydrochloric acid at reflux overnight. The free base was liberated with sodium hydroxide and purified by preparative chromatography, eluting with 90:10 chloroform:methanol: MS (m+1)=400.5.

Workup

  1. temperatureat reflux overnight
  2. custompurified by preparative chromatography
  3. washeluting with 90:10 chloroform

Sources & evidence

ORD record
ord-a2df3f45d6ba47709742312c89b88617
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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