Acetic Acid → HCID 44331444, compound

HRID 1634815Notes

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][C:46]([F:49])=[CH:45][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+]>>[F:17][C:18]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:19]=1[CH2:20][N:21]([CH:42]([CH3:44])[CH3:43])[C:22](=[O:23])[NH:24][C:25]1[CH:30]=[CH:29][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:27][CH:26]=1

Participants

Reactant 4

HCID 176Acetic Acid

HCID 5003444Sodium cyanoborohydride

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

HCID 18678592HCID 18678592, compound

Product 1

HCID 44331444HCID 44331444, compoundYield 29.3%

Procedure

The title compound was prepared from N-[5-(2-amino-1-{R}-hydroxyethyl)-2-hydroxyphenyl]-methanesulfonamide (0.154 g, 0.63 mmol), 1-(2,5-difluoro-benzyl)-3-[4-(4-formyl-piperidine-1-sulfonyl)-phenyl]-1-isopropyl-urea (1.0 mmol), glacial acetic acid (0.036 g, 0.63 mmol) and sodium cyanoborohydride (0.039 g, 0.63 mmol) according to the general procedure used for example 84 (Step E) to give the final product (0.131 g).

Sources & evidence

ORD record: ord-5b46259cc9c24067bc48588cfe7c8da9
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506901B2

Reaction notes

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