Hydrochloric Acid → HCID 50913853, compound

HRID 75978Notes

Reaction equation

HRID 75978 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:30]=[CH:29][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:18]=[C:19]([O:21][C@@H:22]4[CH2:26][CH2:25][N:24]([CH3:27])[C:23]4=[O:28])[CH:20]=3)[C:15]([OH:17])=O)=[CH:9][CH:8]=2)=[N:4][N:3]=1.N#N.CCN=C=NCCCN(C)C.Cl.[NH2:45][C:46]1[S:47][CH:48]=[CH:49][N:50]=1>C(Cl)Cl>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:18]=[C:19]([O:21][C@@H:22]4[CH2:26][CH2:25][N:24]([CH3:27])[C:23]4=[O:28])[CH:20]=3)[C:15]([NH:45][C:46]3[S:47][CH:48]=[CH:49][N:50]=3)=[O:17])=[CH:29][CH:30]=2)=[N:4][N:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 21552-AminothiazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68107027(R)-(+)-3-[4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy]-5-[(1-methyl-2-oxo-pyrrolidin-3-yl)oxy]benzoic acid2×

Product 1

HCID 50913853HCID 50913853, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of (R)-(+)-3-[4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy]-5-[(1-methyl-2-oxo-pyrrolidin-3-yl)oxy]benzoic acid (0.2 g) (Intermediate 18) in dry DCM in single necked round bottomed flask fitted with stop cock with N2(g) balloon, N,N′-dimethylamino pyridine (0.060 g) followed by EDCI. HCl (0.23 g) were added at room temperature. After stirring at the same temperature for 15 min, 2-aminothiazole (0.054 g) was added and stirring was continued for 16 h. Progress of reaction was monitored by TLC. After completion, reaction mixture was diluted with DCM (20 mL), washed with dil HCl (5 mL, 0.05 N), saturated sodium bicarbonate solution, water and brine, dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to get crude brown solid (0.080 g). The crude brown solid was purified by solvent trituration.

Workup

  1. stirringstirring
  2. waitwas continued for 16 h
  3. customProgress of reaction
  4. customAfter completion, reaction mixture
  5. washwashed with dil HCl (5 mL, 0.05 N), saturated sodium bicarbonate solution, water and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-17a898fe21d94b66847bef495ee0e6c9
Source dataset
uspto-grants-2014_09
Patent number
US08835469B2

Reaction notes

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