Acetic Acid → N-(5-{(1R)-2-[(1-{4-{3-(2,6-Difluoro-benzyl)-3-isopropyl-ureido]-benzenesulfonyl}-piperidin-4-ylmethyl)-amino]-1-hydroxy-ethyl}-2-hydroxy-phenyl)-methanesulfonamide

HRID 1634807Notes

Reaction equation

HRID 1634807 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[F:17][C:18]1[CH:48]=[CH:47][CH:46]=[C:45]([F:49])[C:19]=1[CH2:20][N:21]([CH:42]([CH3:44])[CH3:43])[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([N:34]2[CH2:39][CH2:38][CH:37]([CH:40]=O)[CH2:36][CH2:35]2)(=[O:33])=[O:32])=[CH:27][CH:26]=1)=[O:23].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[F:49][C:45]1[CH:46]=[CH:47][CH:48]=[C:18]([F:17])[C:19]=1[CH2:20][N:21]([CH:42]([CH3:44])[CH3:43])[C:22](=[O:23])[NH:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([N:34]2[CH2:35][CH2:36][CH:37]([CH2:40][NH:1][CH2:2][C@@H:3]([C:5]3[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=3)[OH:4])[CH2:38][CH2:39]2)(=[O:33])=[O:32])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 186785251-(2,6-Difluoro-benzyl)-3-[4-(4-formyl-piperidine-1-sulfonyl)-phenyl]-1-isopropyl-urea

Product 1

HCID 10190362N-(5-{(1R)-2-[(1-{4-{3-(2,6-Difluoro-benzyl)-3-isopropyl-ureido]-benzenesulfonyl}-piperidin-4-ylmethyl)-amino]-1-hydroxy-ethyl}-2-hydroxy-phenyl)-methanesulfonamideYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-[5-(2-amino-1-{R}-hydroxyethyl)-2-hydroxyphenyl]-methanesulfonamide (0.159 g, 0.65 mmol), 1-(2,6-difluoro-benzyl)-3-[4-(4-formyl-piperidine-1-sulfonyl}-phenyl]-1-isopropyl-urea (0.6 mol),and glacial acetic acid (0.037 g, 0.65 mmol) in 5 mL methanol was stirred for 1 hour over 4A molecular sieves. In one portion sodium cyanoborohydride (0.041 g, 0.65 mmol) was added and the mixture stirred over night at ambient temperature. The sieves were filtered and the filtrate was preabsorbed on silica gel. The solids were purified by flash chromatography (CH2Cl2—CH3OH, 19:1) to give 0.12 g of product as an off white solid.

Workup

  1. filtrationThe sieves were filtered
  2. customthe filtrate was preabsorbed on silica gel
  3. customThe solids were purified by flash chromatography (CH2Cl2—CH3OH, 19:1)

Sources & evidence

ORD record
ord-f8a339e6ce774e488cfdb5f2bcb9346c
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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