Ammonia → HCID 67199010, compound

HRID 1948746Notes

Reaction equation

HRID 1948746 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:20])[CH:5]=[C:4]([CH3:27])[N:3]=1.[NH3:28]>C1COCC1.CO>[CH3:27][C:4]1[CH:5]=[C:6]([S:8][CH2:9][C:10]2[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:20])[N:7]=[C:2]([NH2:28])[N:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 87552357HCID 87552357, compound

Product 1

HCID 67199010HCID 67199010, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of Example 85 (100 mg, 0.26 mmol) in THF (1 mL) was added 7N ammonia in methanol (5 mL). The reaction mixture was heated in a microwave at 120° C. for 1 h and concentrated in vacuo. Purification by preparative HPLC (Method 1) gave the title compound as an off-white solid (24 mg, 20%). δH (DMSO-d6) 8.60 (s, 1H), 8.27 (s, 1H), 7.84 (d, J 8.1 Hz, 1H), 7.66-7.70 (m, 2H), 7.60-7.65 (m, 1H), 7.45-7.58 (m, 3H), 6.61 (br s, 2H), 6.28 (s, 1H), 4.54 (s, 2H), 2.69 (s, 3H), 2.08 (s, 3H). LCMS (ES+) 373.2 (M+H)+, RT 2.99 minutes (Method 3).

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by preparative HPLC (Method 1)

Sources & evidence

ORD record
ord-a6d7ccc748f249aaad41bbbacb6ff64d
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

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