Benzenesulfonic Acid → HCID 58346321, compound

HRID 2096367Notes

Reaction equation

HRID 2096367 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([C:10]2[CH:19]=[C:18]([CH3:20])[C:13]3[NH:14][C:15](=[O:17])[O:16][C:12]=3[CH:11]=2)=[O:9])[CH:3]=1.[NH2:21][C:22]1[CH:23]=[C:24]2[C:37](=[CH:38][CH:39]=1)[CH2:36][C:26]1([C:34]3[C:29](=[N:30][CH:31]=[CH:32][CH:33]=3)[NH:28][C:27]1=[O:35])[CH2:25]2.C1(S(O)(=O)=O)C=CC=CC=1>CC(O)CCC>[CH3:20][C:18]1[C:13]2[NH:14][C:15](=[O:17])[O:16][C:12]=2[CH:11]=[C:10]([C:8]([C:4]2[CH:3]=[C:2]([NH:21][C:22]3[CH:23]=[C:24]4[C:37](=[CH:38][CH:39]=3)[CH2:36][C:26]3([C:34]5[C:29](=[N:30][CH:31]=[CH:32][CH:33]=5)[NH:28][C:27]3=[O:35])[CH2:25]4)[N:7]=[CH:6][N:5]=2)=[O:9])[CH:19]=1

Participants

5

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 581812066-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-oneHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 58346321HCID 58346321, compound

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

144 mg (0.500 mmol) 6-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one, 126 mg (0.500 mmol) 5-amino-1,3-dihydrospiro[inden-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one and 16.1 mg (0.100 mmol) benzenesulphonic acid were combined in 5.0 mL 2-pentanol and refluxed for 4 h. The reaction mixture was evaporated down, the residue was triturated with PE, suction filtered and washed with PE. The residue was purified by preparative HPLC, the fractions containing the product were combined and the organic solvent was eliminated i.vac. The aqueous phase was neutralised by the addition of 1N aqueous NaOH solution. The product precipitated as a solid was filtered off, washed with water and dried.

Workup

  1. temperaturerefluxed for 4 h
  2. customThe reaction mixture was evaporated down
  3. customthe residue was triturated with PE, suction
  4. filtrationfiltered
  5. washwashed with PE
  6. customThe residue was purified by preparative HPLC
  7. additionthe fractions containing the product
  8. additionThe aqueous phase was neutralised by the addition of 1N aqueous NaOH solution
  9. customThe product precipitated as a solid
  10. filtrationwas filtered off
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-68ec62dfd40f49a08f223c0874f9c878
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

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