Hydrochloric Acid → HCID 25018095, compound

HRID 1944511Notes

Reaction equation

HRID 1944511 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:15][CH2:16][C:17]3[S:18][CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:28])[N:21]=3)[CH:11]=2)[CH:6]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:20]1[N:21]=[C:17]([CH2:16][NH:15][C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=[CH:13]3)[S:18][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59187441HCID 59187441, compound

Product 1

HCID 25018095HCID 25018095, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude 6-{[4-(2-chloro-phenyl)-thiazol-2-ylmethyl]-amino}-naphthalene-2-carboxylic acid methyl ester from Step A is dissolved in THF (1 mL). A solution of 1 M LiOH in H2O (1 mL) is added and the mixture is stirred for 12 h at rt. The mixture is acidified with 1 M HCl (1 mL) and extracted into EtOAc (20 mL). The organic layer is dried (MgSO4), filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford the title compound G1 as a white solid: MS calcd. for C21H16ClN2O2S (M+H+) 395.9. found 396.0.

Workup

  1. extractionextracted into EtOAc (20 mL)
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on reverse phase HPLC (H2O/MeCN gradient)

Sources & evidence

ORD record
ord-17498eb4ad4e4912ad94835b7297e727
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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