Acetic Acid → HCID 10305352, compound

HRID 1634816Notes

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][C:44]([F:47])=[CH:43][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:17][C:18]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][C:19]=1[CH2:20][N:21]([CH3:42])[C:22]([NH:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([N:34]2[CH2:39][CH2:38][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])[CH2:36][CH2:35]2)(=[O:32])=[O:33])=[CH:29][CH:30]=1)=[O:23]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 5003444Sodium cyanoborohydride

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

HCID 18678542HCID 18678542, compound

Product 1

HCID 10305352HCID 10305352, compoundYield 37.4%

Procedure

The title compound was prepared from N-[5-(2-amino-1-{R}-hydroxyethyl)-2-hydroxyphenyl]-methanesulfonamide (0.130 g, 0.53 mmol), 1-(2,5-difluoro-benzyl)-3-[4-(4-formyl-piperidine-1-sulfonyl)-phenyl]-1-methyl-urea (0.8 mmol), glacial acetic acid (0.029 mL, 0.5 mmol) and sodium cyanoborohydride (0.031 g, 0.5 mmol) according to the general procedure used for example 84 (Step E) to give the final product (0.135 g).

Sources & evidence

ORD record: ord-ebc263fe59fd46a9b85abb203c9dfb09
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506901B2

Reaction notes

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