Ammonia → HCID 68584087, compound

HRID 2234797Notes

Reaction equation

HRID 2234797 reaction equation
Cl[C:2]1[C:3]2[C:17]([I:18])=[CH:16][N:15]([C@@H:19]3[O:25][C@H:24]([CH2:26][OH:27])[C@@H:22]([OH:23])[C@@:20]3([CH3:28])[OH:21])[C:4]=2[N:5]=[C:6]([NH:8]C(=O)C(C)(C)C)[N:7]=1.[NH3:29]>>[NH2:8][C:6]1[N:7]=[C:2]([NH2:29])[C:3]2[C:17]([I:18])=[CH:16][N:15]([C@@H:19]3[O:25][C@H:24]([CH2:26][OH:27])[C@@H:22]([OH:23])[C@@:20]3([CH3:28])[OH:21])[C:4]=2[N:5]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86612907HCID 86612907, compound

Product 1

HCID 68584087HCID 68584087, compound

Procedure

A mixture of the compound from Step B (2.92 g, 5.6 mmol) and anhydrous liquid ammonia (50 mL) was heated in a stainless steel autoclave at 110° C. for 1d, then cooled and the solvent evaporated. The residue was treated with MeOH to yield 0.30 g of 15.4. The filtrate was evaporated and purified on silica gel column with CH2Cl2/MeOH (20/1) to furnish additional 1.52 g of the target compound (total yield 77%).

Workup

  1. temperaturecooled
  2. customthe solvent evaporated
  3. additionThe residue was treated with MeOH

Sources & evidence

ORD record
ord-0b63f5b7f23c40179eea905766143463
Source dataset
uspto-grants-2010_05
Patent number
US07713941B2

Reaction notes

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