Hydrochloric Acid → HCID 86287760, compound

HRID 633609Notes

Reaction equation

HRID 633609 reaction equation
C[O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:11]([C:12]3[CH:17]=[C:16]([CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:15]=[CH:14][C:13]=3[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:10][N:9]([CH3:30])[C:8]=12.Cl>CO>[CH3:30][N:9]1[C:8]2[C:3](=[O:2])[NH:4][CH:5]=[CH:6][C:7]=2[C:11]([C:12]2[CH:17]=[C:16]([CH2:18][S:19]([CH3:22])(=[O:20])=[O:21])[CH:15]=[CH:14][C:13]=2[NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 90387876HCID 90387876, compound

Product 1

HCID 86287760HCID 86287760, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of Example 203A (0.062 g, 0.147 mmol) in methanol (1 mL) was treated with hydrogen chloride solution (4 M in 1,4-dioxane, 1 mL, 4 mmol) and heated at 75° C. for 2.5 hours. Additional hydrogen chloride solution (4 M in 1,4-dioxane, 1 mL, 4 mmol) was added and heating was continued for another 3.5 hours. The reaction mixture was then concentrated and the residue was purified by preparative HPLC on a Phenomenex Luna C8(2) 5 μm 100 Å AXIA column (30 mm×75 mm) A gradient of 20-100% acetonitrile (A) and 10 mM ammonium acetate in water (B) was used, at a flow rate of 50 mL/minute (0-0.5 minutes 20% A, 0.5-7.0 minutes linear gradient 20-95% A, 7.0-10.0 minutes 100% A, 10.0-12.0 minutes linear gradient 100-20% A to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 10.89 (d, J=5.19 Hz, 1H), 8.08 (m, 1H), 7.98 (d, J=8.24 Hz, 1H), 7.89 (s, 1H), 7.47 (m, 1H), 7.42 (s, 1H), 7.34 (d, J=2.14 Hz, 1H), 7.27 (dd, J=8.24, 2.14 Hz, 1H), 6.79 (dd, J=6.71, 5.80 Hz, 1H), 6.76 (d, J=8.24 Hz, 1H), 6.70 (m, 1H), 6.25 (d, J=6.71 Hz, 1H), 4.45 (s, 2H), 4.09 (s, 3H), 2.93 (s, 3H). MS (ESI+) m/z 409.1 (M+H)+.

Workup

  1. temperatureheating
  2. concentrationThe reaction mixture was then concentrated
  3. customthe residue was purified by preparative HPLC on a Phenomenex Luna C8(2) 5 μm 100 Å AXIA column (30 mm×75 mm) A gradient of 20-100% acetonitrile (A) and 10 mM ammonium acetate in water (B)
  4. custom0-0.5 minutes 20% A, 0.5-7.0 minutes
  5. customlinear gradient 20-95% A, 7.0-10.0 minutes 100% A, 10.0-12.0 minutes

Sources & evidence

ORD record
ord-a7770bb1c3da47dfb3e13a301e7b61e2
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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