Hydrochloric Acid → HCID 22467265, compound

HRID 1934628Notes

Reaction equation

HRID 1934628 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:15]([C:31]3[CH:39]=[C:38]([O:40][CH3:41])[C:34]4[O:35][CH2:36][O:37][C:33]=4[CH:32]=3)[C:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=3[O:29][CH3:30])(=[O:21])=[O:20])=[O:17])=[CH:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)=[O:4].O.Cl>C(O)C.O1CCOCC1>[OH:4][CH2:3][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:15]([C:31]3[CH:39]=[C:38]([O:40][CH3:41])[C:34]4[O:35][CH2:36][O:37][C:33]=4[CH:32]=3)[C:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=3[O:29][CH3:30])(=[O:21])=[O:20])=[O:17])=[CH:10][N:11]2[CH3:14])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 22467205HCID 22467205, compound

Product 1

HCID 22467265HCID 22467265, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium borohydride (9 mg) was added to a suspension of 6-formyl-3-{1-(7-methoxy-1,3-benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-1H-indole (from Example 96, 130 mg, 0.24 mmol) in a mixture of ethanol (3 ml) and 1,4-dioxane (3 ml) at ambient temperature. Stirring was continued for 1.5 hours, and then water was added dropwise until a solution was achieved. After carefully acidifying with drops of concentrated hydrochloric acid, the solvents were evaporated in vacuo. The residue was partitioned between ethyl acetate and water, and the organic layer was separated and rewashed with water. The organic layer was dried (magnesium sulphate) and the solvents removed in vacuo. The residue was crystallised from a mixture of methanol and diethyl ether to give the title compound (105 mg).

Workup

  1. customthe solvents were evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried (magnesium sulphate)
  5. customthe solvents removed in vacuo
  6. customThe residue was crystallised from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-842aee97f86e4e1a8049ae1244bc3aee
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Reaction notes

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