Benzenesulfonic Acid → 3,4-dimethyl-6-(6-(2'-oxo-1,1',2',3-tetrahydrospiro[inden-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidin-4-carbonyl)benzo[d]oxazol-2(3H)-one

HRID 2096369Notes

Reaction equation

HRID 2096369 reaction equation
C1(S(O)(=O)=O)C=CC=CC=1.[NH2:11][C:12]1[CH:13]=[C:14]2[C:27](=[CH:28][CH:29]=1)[CH2:26][C:16]1([C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]1=[O:25])[CH2:15]2.Cl[C:31]1[N:36]=[CH:35][N:34]=[C:33]([C:37]([C:39]2[CH:49]=[C:48]([CH3:50])[C:42]3[N:43]([CH3:47])[C:44](=[O:46])[O:45][C:41]=3[CH:40]=2)=[O:38])[CH:32]=1>CC(O)CCC>[CH3:47][N:43]1[C:42]2[C:48]([CH3:50])=[CH:49][C:39]([C:37]([C:33]3[CH:32]=[C:31]([NH:11][C:12]4[CH:13]=[C:14]5[C:27](=[CH:28][CH:29]=4)[CH2:26][C:16]4([C:24]6[C:19](=[N:20][CH:21]=[CH:22][CH:23]=6)[NH:18][C:17]4=[O:25])[CH2:15]5)[N:36]=[CH:35][N:34]=3)=[O:38])=[CH:40][C:41]=2[O:45][C:44]1=[O:46]

Participants

5

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 581811626-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-oneHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 583463223,4-dimethyl-6-(6-(2'-oxo-1,1',2',3-tetrahydrospiro[inden-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidin-4-carbonyl)benzo[d]oxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

16.0 mg (0.100 mmol) benzenesulphonic acid were added to 126 mg (0.500 mmol) 5-amino-1,3-dihydrospiro[inden-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one and 152 mg (0.500 mmol) 6-(6-chloro-pyrimidin-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one in 5.0 mL of 2-pentanol and boiled for 4 h. The reaction mixture was evaporated down and purified by preparative HPLC. The fractions containing the product were combined, the organic solvent was eliminated i.vac. and the aqueous phase remaining was neutralised with 1M aqueous NaOH solution. The product precipitated as a solid was suction filtered, washed with water and dried i. vac.

Workup

  1. customThe reaction mixture was evaporated down
  2. custompurified by preparative HPLC
  3. additionThe fractions containing the product
  4. customThe product precipitated as a solid
  5. filtrationfiltered
  6. washwashed with water
  7. customdried i

Sources & evidence

ORD record
ord-0d50a0d3c58a4faa9c2fdd511a3c7841
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

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