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Hydrochloric Acid → HCID 22467265, compound

HRID 381336
Notes
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Reaction equation

HRID 381336 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 702
Ethanol
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

Sodium borohydride (9 mg) was added to s 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-55fd0dd8296d42c486fdf5fb275152b8
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06306852B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes