Water → HCID 67444860, compound

HRID 1666982Notes

Reaction equation

HRID 1666982 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C@@H:9]([C:15]2[N:16]=[CH:17][N:18]([CH2:20][C:21]3[CH:25]=[C:24]([C:26]4[S:27][C:28]([Cl:31])=[CH:29][CH:30]=4)[O:23][N:22]=3)[CH:19]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.O>Cl>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C@@H:9]([C:15]2[N:16]=[CH:17][N:18]([CH2:20][C:21]3[CH:25]=[C:24]([C:26]4[S:27][C:28]([Cl:31])=[CH:29][CH:30]=4)[O:23][N:22]=3)[CH:19]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 67444646Ethyl (S)-3-(6-aminopyridin-3-yl)-2-{1-[5-(5-chlorothiophen-2-yl)isoxazol-3-ylmethyl]-1H-imidazol-4-yl}propionate

Product 1

HCID 67444860HCID 67444860, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent3×

Procedure

A solution of 0.11 g (0.24 mmol) of ethyl (S)-3-(6-aminopyridin-3-yl)-2-{1-[5-(5-chlorothiophen-2-yl)isoxazol-3-ylmethyl]-1H-imidazol-4-yl}propionate in 2 ml of semi-concentrated hydrochloric acid was stirred at RT for 24 h. The reaction mixture was freeze-dried and purified by preparative HPLC. The fractions of value obtained were combined and freeze-dried with 2 equivalents (eq) of 1N HCl (1×) and with 1 eq of 1N HCl and water (1×). This gave 0.077 g (69%) of the title compound as the hydrochloride.

Workup

  1. customThe reaction mixture was freeze-dried
  2. custompurified by preparative HPLC
  3. customThe fractions of value obtained

Sources & evidence

ORD record
ord-ab0c73dbdccc434ead1ba861ff9c76f2
Source dataset
uspto-grants-2011_10
Patent number
US08044208B2

Reaction notes

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