Hydrochloric Acid → HCID 178524197, compound

HRID 1946994Notes

Reaction equation

HRID 1946994 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[C:12]2[CH:13]=[CH:14][N:15]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH:27]4[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]4)[N:21]=3)[C:16]=2[CH:17]=[CH:18][CH:19]=1)=[O:10].O.Cl>C1COCC1.CO>[OH:33][C@H:30]1[CH2:31][CH2:32][C@H:27]([NH:26][C:22]2[N:21]=[C:20]([N:15]3[C:16]4[CH:17]=[CH:18][CH:19]=[C:11]([C:9]([OH:10])=[O:8])[C:12]=4[CH:13]=[CH:14]3)[CH:25]=[CH:24][N:23]=2)[CH2:28][CH2:29]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 24958441HCID 24958441, compound

Product 1

HCID 178524197HCID 178524197, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LAH (327 mg, 13.6 mmol) was added to a suspension of 1-[2-(4-hydroxycyclohexylamino)-pyrimidin-4-yl]-1H-indole-4-carboxylic acid methyl ester (1.0 g, 2.7 mmol) in a mixture of THF (4 mL), water (4 mL) and MeOH (1 mL). The reaction mixture was stirred at RT for 16 h, then evaporated under reduced pressure to give a beige solid. Aqueous HCl (1 M, 14 mL) was added to the residue, and the resulting mixture was stirred and evaporated under reduced pressure. The residue was triturated with MeOH to give trans-1-[2-(4-hydroxycyclohexylamino)-pyrimidin-4-yl]-1H-indole-4-carboxylic acid (700 mg) as an off-white solid. MS=353 [M+H]+; MP=259.0-261.0° C.

Workup

  1. customevaporated under reduced pressure
  2. customto give a beige solid
  3. stirringthe resulting mixture was stirred
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with MeOH

Sources & evidence

ORD record
ord-6bd0aaaef6fc4c3c804a424c69036fe3
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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