Lithium Hydroxide → HCID 66699087, compound

HRID 1096038Notes

Reaction equation

HRID 1096038 reaction equation
C1N2CCN(CC2)C1.[Cl:9][C:10]1[C:11](Cl)=[N:12][CH:13]=[C:14]([CH:19]=1)[C:15]([O:17]C)=[O:16].[Cl:21][C:22]1[CH:23]=[C:24]([OH:46])[CH:25]=[CH:26][C:27]=1[CH:28]([CH3:45])[C:29]([OH:44])([C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[N:40]=[CH:39][CH:38]=[N:37]2)[C:30]([F:33])([F:32])[F:31].[Li+].[OH-]>CN(C=O)C.C(N(CC)CC)C>[Cl:9][C:10]1[C:11]([O:46][C:24]2[CH:25]=[CH:26][C:27]([CH:28]([CH3:45])[C:29]([OH:44])([C:34]3[CH:35]=[C:36]4[C:41](=[CH:42][CH:43]=3)[N:40]=[CH:39][CH:38]=[N:37]4)[C:30]([F:31])([F:32])[F:33])=[C:22]([Cl:21])[CH:23]=2)=[N:12][CH:13]=[C:14]([CH:19]=1)[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 9237DabcoHCID 2782166Methyl 5,6-DichloronicotinateHCID 66699191HCID 66699191, compound

Product 1

HCID 66699087HCID 66699087, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

DABCO (2 mg) was added to a mixture of methyl 5,6-dichloronicotinate (27 mg, CAS. Reg. No. 56055-54-0), 3-chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinoxalin-6-yl-propyl)-phenol (50 mg), and triethylamine (17 mg) in DMF (5 ml). The mixture was stirred at room temperature overnight. Aqueous LiOH solution (1N, 1 ml) was added and then stirred for 2 hours to hydrolyze the intermediate ester. The mixture was purified by prep. HPLC (C18-column, solvent gradient 20-98% CH3CN in 0.1% HCOOH[aq]) to give the title compound (10 mg) as a white foam. MS (m/e)=536.1 [M+H+].

Workup

  1. stirringstirred for 2 hours
  2. customThe mixture was purified by prep

Sources & evidence

ORD record
ord-46da5ed49731460582a23bfab0b1b9e6
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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