Benzenesulfonic Acid → HCID 56654395, compound

HRID 2178180Notes

Reaction equation

HRID 2178180 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10]2[N:15]=[C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]4[O:24][C:23](=[O:25])[NH:22][C:21]=4[CH:26]=3)[C:13]([CH3:27])=[CH:12][N:11]=2)=[CH:4][C:3]=1[O:28][CH3:29].[C:30]1([S:36]([OH:39])(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CO>[S:36]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([OH:39])(=[O:38])=[O:37].[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10]2[N:15]=[C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]4[O:24][C:23](=[O:25])[NH:22][C:21]=4[CH:26]=3)[C:13]([CH3:27])=[CH:12][N:11]=2)=[CH:4][C:3]=1[O:28][CH3:29]

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 468516252(3H)-Benzoxazolone, 5-[[2-[(4-fluoro-3-methoxy-5-methylphenyl)amino]-5-methyl-4-pyrimidinyl]amino]-

Product 1

HCID 56654395HCID 56654395, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The benzenesulfonic (besylate) salt of the illustrated product was obtained as follows: Into a MeOH (400 mL) suspension of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one (free base; 39.5 g, 100 mmol), with stirring, benzenesulfonic acid (16.61 g, 105 mmol) was added (note: the reaction mixture turned into an almost homogeneous light brown solution briefly, ppts appeared shortly afterwards). The cloudy solution was stirred at 50° C. for 90 min, cool to rt, solid was collected by filtration, washing with EtOAc (˜150 mL×2), and was further dried under high vac. Compound 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one besylate was obtained as a very light tan color solid: 52.09 g (94% yield); 1H NMR (300 MHz, DMSO) δ 11.99 (br s, 1H), 11.80 (s, 1H), 10.05 (s, 1H), 9.81 (s, 1H), 7.87 (s, 1H), 7.65-7.62 (m, 2H), 7.39-7.33 (m, 4H), 7.29-7.26 (m, 2H), 6.96 (br d, J=7.4 Hz, 1H), 6.91 (br d, J=5.6 Hz, 1H), 3.66 (s, 3H), 2.20 (s, 3H), 2.06 (s, 3H); LRMS (M+) m/z 396.15

Workup

  1. stirringThe cloudy solution was stirred at 50° C. for 90 min
  2. filtrationsolid was collected by filtration
  3. washwashing with EtOAc (˜150 mL×2)
  4. customwas further dried under high vac

Sources & evidence

ORD record
ord-c414a1a5db844115af3f71e75bb1b2b1
Source dataset
uspto-grants-2015_06
Patent number
US09067925B2

Reaction notes

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