Hydrochloric Acid → HCID 178513745, compound

HRID 1527566Notes

Reaction equation

HRID 1527566 reaction equation
[Cl:1][C:2]1[C:3]([F:34])=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][NH:6][C:7]([C@@H:9]1[CH2:13][C@@H:12]([F:14])[CH2:11][N:10]1[C:15](=[O:30])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([OH:26])[CH:24]=2)[C:19]([C:27]([NH2:29])=[O:28])=[CH:18]1)=[O:8].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:42][C:43]1[NH:47][N:46]=[N:45][N:44]=1.Cl>CS(C)=O.O>[Cl:1][C:2]1[C:3]([F:34])=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][NH:6][C:7]([C@@H:9]1[CH2:13][C@@H:12]([F:14])[CH2:11][N:10]1[C:15](=[O:30])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH2:42][C:43]3[NH:47][N:46]=[N:45][N:44]=3)[CH:24]=2)[C:19]([C:27]([NH2:29])=[O:28])=[CH:18]1)=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 68283145HCID 68283145, compoundHCID 178478452HCID 178478452, compound

Product 1

HCID 178513745HCID 178513745, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 1-{2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-6-hydroxy-1H-indole-3-carboxylic acid amide Example 578 (148 mg, 0.283 mmol) in DMSO (3 mL) was treated with Cs2CO3 (0.28 g, 0.85 mmol). The mixture was stirred at RT for 5 min, followed by addition of 5-(chloromethyl)-1H-tetrazole (35 mg, 0.098 mmol) and stirring at RT for 36 h. The reaction mixture was neutralised by addition of 1N HCl. Water was then added to the mixture to form a precipitate. The solid material was filtered off, washed with water, and dried in vacuo to afford the title compound as a solid. MS (LC/MS): 573 [M+H]+; tR (HPLC conditions k): 2.92 min.

Workup

  1. stirringstirring at RT for 36 h
  2. customto form a precipitate
  3. filtrationThe solid material was filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a5011499d39d4ac09b19f8ad691c32ab
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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