Ammonia → HCID 178508010, compound

HRID 970657Notes

Reaction equation

HRID 970657 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[N:12]=[C:11]([CH2:13][OH:14])[NH:10][C:7]2=[N:8][CH:9]=1)([O-])=O.N>Cl>[NH2:1][C:4]1[CH:5]=[C:6]2[N:12]=[C:11]([CH2:13][OH:14])[NH:10][C:7]2=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178526790HCID 178526790, compound

Product 1

HCID 178508010HCID 178508010, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

Stannous chloride dihydrate (1.6 g, 0.0070 mol) was added in one portion to a stirred solution of (6-Nitro-3H-imidazo[4,5-b]pyridin-2-yl)-methanol (450 mg, 0.0023 mol) in 10% aqueous hydrochloric acid (20 mL) at 50° C. The mixture was stirred at 50° C. for approx. 2 hours then allowed to cool to room temperature. The mixture was cooled further to 0° C. and then basified to ca. pH 8 using conc. NH3 solution. The aqueous layer was then filtered through Celite® to remove tin salts and the filtrate was concentrated under vacuum to leave a crude solid (380 mg; yield assumed quantitative) which was used directly in the next step (amide formation).

Workup

  1. temperatureto cool to room temperature
  2. temperatureThe mixture was cooled further to 0° C.
  3. filtrationThe aqueous layer was then filtered through Celite®
  4. customto remove tin salts
  5. concentrationthe filtrate was concentrated under vacuum
  6. customto leave a crude
  7. customsolid (380 mg; yield assumed quantitative) which

Sources & evidence

ORD record
ord-4294c3c9117444a59575d5b2a23c5f02
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Reaction notes

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