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

tert-Butanol → (6'-Chloro-2-methyl-[3,4']bipyridinyl-3'-yl)-carbamic acid tert-butyl ester

HRID 347682
Notes
Print preview

Reaction equation

HRID 347682 reaction equation
FC(F)(F)C1C=C(C(C)(C)[C:14]([N:16](C)[C:17]2[CH:18]=[N:19][C:20](N3CCN(C)CC3)=[CH:21][C:22]=2[C:23]2[C:24]([CH3:29])=[N:25][CH:26]=[CH:27][CH:28]=2)=[O:15])C=C(C(F)(F)F)C=1.[Cl:42]C1N=CC(C(O)=O)=C(C2C(C)=NC=CC=2)C=1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:83]([OH:87])([CH3:86])([CH3:85])[CH3:84]>>[C:83]([O:87][C:14](=[O:15])[NH:16][C:17]1[CH:18]=[N:19][C:20]([Cl:42])=[CH:21][C:22]=1[C:23]1[C:24]([CH3:29])=[N:25][CH:26]=[CH:27][CH:28]=1)([CH3:86])([CH3:85])[CH3:84]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 115560662-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-[2-methyl-6'-(4-methyl-piperazin-1-yl)-[3,4']bipyridinyl-3'-yl]-isobutyramideHCID 210836376'-Chloro-2-methyl-[3,4']bipyridinyl-3'-carboxylic acid

Product 1

HCID 58694598
(6'-Chloro-2-methyl-[3,4']bipyridinyl-3'-yl)-carbamic acid tert-butyl ester

Procedure

2-(3,5-Bis-trifluoromethyl-phenyl)-N-methyl-N-[2-methyl-6′-(4-methyl-piperazin-1-yl)-[3,4′]bipyridinyl-3′-yl]-isobutyramide of formula I-2 can be prepared as follows: A solution of 6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-carboxylic acid (VI), triethylamine and diphenylphosphoryl azide in tert-butanol is stirred at about 90° C. under argon for 1.5 h. After cooling to room temperature, the solvent is evaporated. The residue is diluted with ethyl acetate and washed with aqueous sodium hydrogencarbonate solution and brine. The organic layer is concentrated and purified to give the compound (6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-yl)-carbamic acid tert-butyl ester of formula VIII.

Workup

  1. customthe solvent is evaporated
  2. additionThe residue is diluted with ethyl acetate
  3. washwashed with aqueous sodium hydrogencarbonate solution and brine
  4. concentrationThe organic layer is concentrated
  5. custompurified

Sources & evidence

ORD record
ord-e923a309dc824efb8302c19cca8fa673
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07176205B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes