Potassium Carbonate → HCID 178490683, compound

HRID 2196824Notes

Reaction equation

HRID 2196824 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:22][CH2:23][OH:24])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ClC(Cl)(Cl)[C:27]([N:29]=C=O)=[O:28].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O>[C:27](=[O:28])([O:24][CH2:23][CH2:22][N:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[S:9]/[C:8]/1=[N:10]\[C:11](=[O:21])[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[NH2:29]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 76400Trichloroacetyl isocyanateHCID 178490682HCID 178490682, compound

Product 1

HCID 178490683HCID 178490683, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 60A (110 mg, 0.298 mmol) in CH2Cl2 (2 mL) was added trichloroacetyl isocyanate (67.4 mg, 0.358 mmol) and the mixture was stirred for 2 hr. The reaction was concentrated and dissolved in methanol (0.5 mL). A solution of potassium carbonate (140 mg, 1.013 mmol) in water was added and the mixture was stirred for 24 hr. The reaction was concentrated, partitioned between ethyl acetate (3×10 mL) and water (10 mL). The organics were combined, dried, filtered, concentrated and the residue was triturated with CH2Cl2 and hexane (1:3). The solid was collected by filtration (80 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.32 (s, 9 H) 3.79 (s, 3 H) 4.29-4.38 (m, 4 H) 6.55 (s, 1 H) 7.10 (d, J=9.12 Hz, 1 H) 7.19 (s, 1 H) 7.44 (dd, J=9.12, 2.78 Hz, 1 H) 7.67 (d, J=2.78 Hz, 1 H); MS (DCI) m/z 412 (M+H)+. Anal calcd C18H22ClN3O4S.0.5H2O: C, 51.36; H, 5.51; N, 9.98. Found: C, 51.23; H, 5.33; N, 9.92.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in methanol (0.5 mL)
  3. stirringthe mixture was stirred for 24 hr
  4. concentrationThe reaction was concentrated
  5. custompartitioned between ethyl acetate (3×10 mL) and water (10 mL)
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue was triturated with CH2Cl2 and hexane (1:3)
  10. filtrationThe solid was collected by filtration (80 mg, 70%)

Sources & evidence

ORD record
ord-74651bc93369475983a55d4fac2c1aad
Source dataset
uspto-grants-2012_12
Patent number
US08338467B2

Reaction notes

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