Hydrochloric Acid → HCID 70224371, compound

HRID 1596401Notes

Reaction equation

HRID 1596401 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][C:11]3[CH:15]=[C:16]([O:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[N:25][CH:26]=4)[CH:17]=[CH:18][C:10]=3[C:9]=2[N:8]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34]COC)[CH:29]=2)[N:7]=1)=[O:5]>O1CCCC1>[CH3:2][O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][C:11]3[CH:15]=[C:16]([O:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[N:25][CH:26]=4)[CH:17]=[CH:18][C:10]=3[C:9]=2[N:8]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)[N:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15550472HCID 15550472, compound

Product 1

HCID 70224371HCID 70224371, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6 N hydrochloric acid (3 ml) was added to a solution in tetrahydrofuran (15 ml) of the 4,5-dihydro-1-(3-methoxymethoxybenzyl)-7-(5-pyrimidinylmethoxy)-[1H]-benz[g]indazole-3-carboxylic acid methyl ester (308 mg, 0.63 m mol) obtained in the step A of Example 27, and this mixture was stirred at room temperature for 3 hours. Thereafter, the reaction mixture was concentrated under reduced pressure. After the addition of ice water (50 ml), the reaction mixture was alkalified with a saturated aqueous solution of sodium bicarbonate and then extracted with chloroform (2×50 ml). After the extract was washed with water and dried, the solvent was distilled off under reduced pressure. The resulting solid residue was washed with ethyl acetate to obtain the desired compound (187 mg, 66%) as a pale-yellow solid.

Workup

  1. customobtained in the step A of Example 27
  2. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  3. additionAfter the addition of ice water (50 ml)
  4. extractionextracted with chloroform (2×50 ml)
  5. washAfter the extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. washThe resulting solid residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-1918c71a27944ca5ac71a40fd5b7de09
Source dataset
uspto-grants-2001_09
Patent number
US06291485B1

Reaction notes

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