Sodium borohydride → N-[(4-methoxyphenyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

HRID 589984Notes

Reaction equation

HRID 589984 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[N:10]\[S:11]([N:14]2[C:19]3([CH2:21][CH2:20]3)[CH2:18][N:17]([C:22]3[C:23]4[CH:30]=[CH:29][NH:28][C:24]=4[N:25]=[CH:26][N:27]=3)[CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][S:11]([N:14]2[C:19]3([CH2:20][CH2:21]3)[CH2:18][N:17]([C:22]3[C:23]4[CH:30]=[CH:29][NH:28][C:24]=4[N:25]=[CH:26][N:27]=3)[CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118649767(NZ)-N-[(4-methoxyphenyl)methylidene]-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide2×

Product 1

HCID 57410101N-[(4-methoxyphenyl)methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(NZ)—N-[(4-methoxyphenyl)methylene]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (intermediate 49) was dissolved in MeOH, added NaBH4 (1 eq) and stirred at rt for 2 h. The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

Workup

  1. customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record
ord-108ea9a49dfd43979bdd23260f3aa0f6
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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