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

Hydrochloric Acid → (S)-2-{[5-(2,4-Difluorophenoxy)-1-isobutyl-1H-indazole-6-carbonyl]-amino}-4-dimethylaminobutyric acid

HRID 1715630
Notes
Print preview

Reaction equation

HRID 1715630 reaction equation
C[Si](C)(C)[O-].[K+].C[O:8][C:9](=[O:41])[C@@H:10]([NH:16][C:17]([C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[N:24][N:25]2[CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:21][C:20]=1[O:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=1[F:40])=[O:18])[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].Cl>C1COCC1>[F:40][C:34]1[CH:35]=[C:36]([F:39])[CH:37]=[CH:38][C:33]=1[O:32][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][C:19]=1[C:17]([NH:16][C@@H:10]([CH2:11][CH2:12][N:13]([CH3:14])[CH3:15])[C:9]([OH:41])=[O:8])=[O:18])[N:25]([CH2:28][CH:29]([CH3:31])[CH3:30])[N:24]=[CH:23]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668039Potassium trimethylsilanolateHCID 57639703HCID 57639703, compound

Product 1

HCID 42611138(S)-2-{[5-(2,4-Difluorophenoxy)-1-isobutyl-1H-indazole-6-carbonyl]-amino}-4-dimethylaminobutyric acidYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Potassium trimethylsilanolate (1.77 g, 13.8 mmol) was added to a solution of (S)-2-{[5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole-6-carbonyl]-amino}-4-dimethylaminobutyric acid methyl ester (3.36 g, 6.88 mmol) in THF (5 mL). The reaction mixture was stirred at room temperature for 4 hours. HCl (17 mL of 4M in dioxane) was added to the mixture before it was concentrated under reduced pressure. The residue was suspended in dichloromethane and filtered. The filtrate was concentrated under reduced pressure to afford 2.23 g of product (68% yield). MS (ESI+) m/z 475 (M+1) detected; 1H NMR (400 mHz, DMSO-D6) δ 8.81 (d, 1H), 8.02 (s, 1H), 7.99 (s, 1H), 7.48 (m, 1H), 7.25 (m, 1H), 7.22 (s, 1H), 7.11 (m, 1H), 4.50 (m, 1H), 4.28 (d, 2H), 3.17 (m, 1H), 3.04 (m, 1H), 2.70 (s, 6H), 2.25 (m, 2H), 2.13 (m, 1H), 0.87 (d, 6H).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9bd7ed1cb36d423ca3ca472bd704b945
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07799782B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes