Acetic Acid → HCID 18678612, compound

HRID 1634811Notes

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:46]=[CH:45][CH:44]=[C:43]([F:47])[C:19]=1[CH2:20][N:21]([CH3:42])[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+]>>[F:47][C:43]1[CH:44]=[CH:45][CH:46]=[C:18]([F:17])[C:19]=1[CH2:20][N:21]([CH3:42])[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][CH: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

Reactant 4

HCID 176Acetic Acid

HCID 5003444Sodium cyanoborohydride

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

HCID 18678744HCID 18678744, compound

Product 1

HCID 18678612HCID 18678612, compoundYield 39.9%

Procedure

The title compound was prepared from N-[5-(2-amino-1-{R}-hydroxyethyl)-2-hydroxyphenyl]-methanesulfonamide (0.126 g, 0.51 mmol), 1-(2,6-Difluoro-benzyl)-3-[4-(4-formyl-piperidine-1-sulfonyl)-phenyl]-1-methyl-urea (0.5 mmol), glacial acetic acid (0.028 g, 0.49 mmol) and sodium cyanoborohydride (0.031 g, 0.49 mmol) according to the general procedure used for example 84 (Step E) to give the final product (0.136 g).

Sources & evidence

ORD record: ord-c42e41922c7943cba730a072eab029ec
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506901B2

Reaction notes

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