Ammonia → HCID 58204890, compound

HRID 1498495Notes

Reaction equation

HRID 1498495 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[N:27]=[CH:26][C:9]2[C:10]3[N:14]([CH2:15][CH2:16][O:17][C:8]=2[CH:7]=1)[CH:13]=[C:12]([C:18]1[N:19]([CH:23]([CH3:25])[CH3:24])[N:20]=[CH:21][N:22]=1)[N:11]=3.[NH3:29]>CO>[CH:23]([N:19]1[C:18]([C:12]2[N:11]=[C:10]3[C:9]4[CH:26]=[N:27][C:6]([O:5][CH2:4][C:3]([NH2:29])=[O:2])=[CH:7][C:8]=4[O:17][CH2:16][CH2:15][N:14]3[CH:13]=2)=[N:22][CH:21]=[N:20]1)([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58204655HCID 58204655, compound

Product 1

HCID 58204890HCID 58204890, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-yloxy]-acetic acid methyl ester (88 mg, 0.23 mmol) was dissolved in a solution of ammonia in methanol (7N, 5 mL) and the reaction mixture heated at 50° C. for 2 h, during which a white precipitate formed. The reaction mixture was concentrated in vacuo and the residue subjected to reverse phase preparative HPLC (C-18, 10-90% MeCN in water, 0.1% formic acid, 25 min gradient) to yield 427 as a white solid (42 mg, 50%). LCMS: RT=2.85 min, [M+H]+=370; 1H NMR (400 MHz, d6-DMSO) 9.07 (1H, s), 7.88 (1H, s), 7.86 (1H, s), 7.41 (1H, s), 7.18 (1H, s), 6.45 (1H, s), 5.87 (1H, sept, J=6.7 Hz), 4.66 (2H, s), 4.60-4.44 (4H, m), 1.44 (6H, d, J=6.7 Hz).

Workup

  1. customformed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customphase preparative HPLC (C-18, 10-90% MeCN in water, 0.1% formic acid, 25 min gradient)

Sources & evidence

ORD record
ord-85b0fb5a50bc4abf8e84940cb7258f85
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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