HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

(S)-2-(4-cyano-2,6-difluorobenzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester → (S)-2-[4-[[3,5-difluoro-4-[(S)-1-propoxycarbonyl-2-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]ethylcarbamoyl]benzylamino]methyl]-2,6-difluorobenzoylamino]-3-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]propionic acid propyl ester

HRID 63751
Notes
Print preview

Reaction equation

HRID 63751 reaction equation
[CH2:1]([O:4][C:5](=[O:38])[C@@H:6]([NH:25][C:26](=[O:37])[C:27]1[C:32]([F:33])=[CH:31][C:30]([C:34]#[N:35])=[CH:29][C:28]=1[F:36])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:10][CH:9]=1)[CH2:2][CH3:3]>C(O)CC>[CH2:1]([O:4][C:5](=[O:38])[C@@H:6]([NH:25][C:26](=[O:37])[C:27]1[C:28]([F:36])=[CH:29][C:30]([CH2:34][NH:35][CH2:34][C:30]2[CH:29]=[C:28]([F:36])[C:27]([C:26](=[O:37])[NH:25][C@H:6]([C:5]([O:4][CH2:1][CH2:2][CH3:3])=[O:38])[CH2:7][C:8]3[CH:9]=[CH:10][C:11]([C:14]4[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=4[CH3:20])=[CH:12][CH:13]=3)=[C:32]([F:33])[CH:31]=2)=[CH:31][C:32]=1[F:33])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:12][CH:13]=1)[CH2:2][CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 86691353(S)-2-(4-cyano-2,6-difluorobenzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

Product 1

HCID 89720749(S)-2-[4-[[3,5-difluoro-4-[(S)-1-propoxycarbonyl-2-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]ethylcarbamoyl]benzylamino]methyl]-2,6-difluorobenzoylamino]-3-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]propionic acid propyl esterYield 39.2%

Reagents, catalysts & solvents 1

HCID 1031
1-Propanol
Solvent

Procedure

To a 100 mL flask containing (S)-2-(4-cyano-2,6-difluorobenzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)phenyl]propionic acid propyl ester (524 mg, 1.0 mmol) dissolved in n-propanol (20 mL) purged with nitrogen was added palladium on carbon (10%, 106 mg). The reaction was sealed, degassed with three exposures to nitrogen and house vacuum, and then exposed to a balloon of hydrogen overnight. The reaction was diluted with EA, degassed again, and exposed to hydrogen overnight. The reaction was filtered through celite, concentrated and purified by HPLC yielding the title compound (204 mg, 19%). ES(+)-LRMS m/e calcd. for C54H57F4N7O10 (M+H)+ 1041, obsd 1041.

Workup

  1. custompurged with nitrogen
  2. additionwas added palladium on carbon (10%, 106 mg)
  3. customThe reaction was sealed
  4. customdegassed with three exposures to nitrogen and house vacuum
  5. customexposed to a balloon of hydrogen overnight
  6. additionThe reaction was diluted with EA
  7. customdegassed again
  8. customexposed to hydrogen overnight
  9. filtrationThe reaction was filtered through celite,
  10. concentrationconcentrated
  11. custompurified by HPLC

Sources & evidence

ORD record
ord-d101ae79daf44e73a29fe5c00293093e
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447035B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes