Hydrochloric Acid → HCID 68778509, compound

HRID 2264516Notes

Reaction equation

HRID 2264516 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][NH:8][C:9]1[N:14]=[C:13]([NH:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:28]=[C:27]([O:29][CH2:30][CH3:31])[C:26]([F:32])=[C:25]([O:33][CH2:34][CH3:35])[CH:24]=3)[CH2:18][CH2:17]2)[N:12]=[C:11]([O:36][CH3:37])[N:10]=1)(C)(C)C.[Li+].[OH-].O.Cl>C1COCC1.CO>[CH2:34]([O:33][C:25]1[CH:24]=[C:23]([CH:28]=[C:27]([O:29][CH2:30][CH3:31])[C:26]=1[F:32])[CH2:22][N:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:13]2[N:12]=[C:11]([O:36][CH3:37])[N:10]=[C:9]([NH:8][CH2:7][C:6]([OH:38])=[O:5])[N:14]=2)[CH2:17][CH2:18]1)[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 68782177HCID 68782177, compound

Product 1

HCID 68778509HCID 68778509, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of {4-[1-(3,5-diethoxy-4-fluoro-benzyl)-piperidin-4-ylamino]-6-methoxy-[1,3,5]triazin-2-ylamino}-acetic acid tert-butyl ester (0.09 g, 0.2 mmol, 1.0 equiv; example 297) in THF/methanol (1:1) (4 mL) was added drop by drop a 1 M solution of LiOH in water (0.42 mL, 0.42 mmol, 2.1 equiv). After 16 h, the reaction mixture was poured into ice water, the pH adjusted to 3-4 with diluted HCl and the mixture extracted three times with dichloromethane/isopropanol (4:1). The combined organic layers were concentrated by evaporation under reduced pressure to yield 0.031 g (32%) of the title compound as a colorless solid. MS (ISN): 477.2 [M−H]−.

Workup

  1. extractionthe mixture extracted three times with dichloromethane/isopropanol (4:1)
  2. concentrationThe combined organic layers were concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ce69d4883e604bcaab48358f92a20655
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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