Ammonia → HCID 23518318, compound

HRID 1836266Notes

Reaction equation

HRID 1836266 reaction equation
Br[C:2]1[N:3]([C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:21])[C:19]=2[N:20]=1)[C@@H:4]1[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@@:5]1([CH3:13])[OH:6].[NH3:22]>>[NH2:22][C:2]1[N:3]([C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:21])[C:19]=2[N:20]=1)[C@@H:4]1[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@@:5]1([CH3:13])[OH:6]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 23518344HCID 23518344, compound

Product 1

HCID 23518318HCID 23518318, compound

Procedure

A solution of the compound from Step A (38 mg, 0.11 mmol) in liquid ammonia (10 mL) was heated in a stainless steel autoclave at 105° C. for 1 d, then cooled and evaporated. The residue was purified by HPLC [C-18 Phenomenex Luna (10 μ; 250×21.2 mm) RP-column; solvents:(A) water, (B) acetonitrile; Linear gradient: 2-35% B in 76 min.] to yield the title compound (12 mg) as a white fluffy material after freeze-drying.

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was purified by HPLC [C-18 Phenomenex Luna (10 μ; 250×21.2 mm) RP-column; solvents:(A) water, (B) acetonitrile; Linear gradient: 2-35% B in 76 min.]

Sources & evidence

ORD record
ord-5e7899689aa54f3fa0c931c35d780b25
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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