Hydrochloric Acid → HCID 69890959, compound

HRID 566406Notes

Reaction equation

HRID 566406 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:19]4[CH:27]=[C:26]([C:28]5[O:29][C:30]([C:33]67OCC(C)(C[O:38]6)C[O:34]7)=[CH:31][CH:32]=5)[N:25]=[CH:24][C:20]=4[N:21]=[CH:22][N:23]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:42]>C1COCC1.O>[ClH:42].[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:19]4[CH:27]=[C:26]([C:28]5[O:29][C:30]([C:33]([OH:38])=[O:34])=[CH:31][CH:32]=5)[N:25]=[CH:24][C:20]=4[N:21]=[CH:22][N:23]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22727422HCID 22727422, compound

Product 1

HCID 69890959HCID 69890959, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(1-Benzylindazol-5-yl)-(6-(5-(4-methyl-2,6,7-trioxa-bicyclo[2,2,2]oct-1-yl)-furan-2-yl]-pyrido-[3,4-d]pyrimidin-4-yl)-amine (0.445 g, 0.81 mmol) was suspended in a mixture of THF (15 ml) and dilute HCl (15 ml) and stirred at room temperature for 18 hours. The mixture was diluted with water to preciptate the intermediate (partial hydrolysis) which was collected by filtration and washed with water. This solid was suspended in a mixture of THF (10 ml) and NaOH (1M, 10 ml) and stirred at room tmperature for 18 hours. The THF was removed in vacuo and the residue was acidified to pH1 with dilute HCl to give the product as an orange solid, which was collected by filtration (0.322 g, 0.645 mmol, 79%); δH [2H6]DMSO 10.63(1H,s), 9.19(1H,s), 8.89(1H,s), 8.64 (1H,s), 8.17-8.22 (2H,m), 7.67-7.80 (2H,m), 7.46 (1H,s), 7.23-7.39 (6H,m), 5.70 (2H,s); m/z (M+1+) 463.

Workup

  1. customthe intermediate (partial hydrolysis) which
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. additionThis solid was suspended in a mixture of THF (10 ml) and NaOH (1M, 10 ml)
  5. stirringstirred at room tmperature for 18 hours
  6. customThe THF was removed in vacuo

Sources & evidence

ORD record
ord-fbf0c67a0463431fac7ca263ed82ad67
Source dataset
uspto-grants-2001_01
Patent number
US06174889B1

Reaction notes

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