Ammonia → HCID 25071652, compound

HRID 1805286Notes

Reaction equation

HRID 1805286 reaction equation
N.C([O:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:26])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH2:25])=[CH:13][CH:12]=2)[CH2:7]1)(=O)C>CO>[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][C:17](=[O:26])[C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][C@H:6]([OH:5])[CH2:7]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 25071653HCID 25071653, compound

Product 1

HCID 25071652HCID 25071652, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonia gas was bubbled into a solution of compound 159 (300 mg, 0.88 mmol) in methanol (10 mL) at 0° C. for 5 min. The reaction mixture was then stirred for 3 hrs at r.t. and concentrated. The residue was purified by flash chromatography using a gradient 75-100% EtOAc in hexanes as an eluent, to afford title compound 160 (135 mg, 51% yield). 1H NMR: (MeOH-d4) δ(ppm): 7.91 (s, 1H), 7.86 (d, 2H, J=7.0 Hz), 7.16 (d, 1H, J=7.8 Hz), 7.05 (t, 1H, J=7.2 Hz), 6.89 (d, 1H, J=8.0 Hz), 6.76 (t, 1H, J=7.6 Hz), 6.62 (d, 2H, J=9.0 Hz), 4.56 (m, 1H), 3.54 (m, 2H), 3.46 (m, 1H), 2.98 (s, 1H), 2.85 (s, 1H), 2.17 (m, 1H), 2.05 (m, 1H), LRMS (ESI): (calc): 297.15 (found) 298.1 (MH+).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2e25cb9e04ab410e82038c40add8f88e
Source dataset
uspto-grants-2013_01
Patent number
US08354445B2

Reaction notes

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