Cesium carbonate → HCID 178467194, compound

HRID 1527567Notes

Reaction equation

HRID 1527567 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](=[O:29])[CH3:28])=[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>CS(C)=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](=[O:29])[CH3:28])=[CH:18]1)=[O:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68283662HCID 68283662, compoundHCID 178478452HCID 178478452, compound

Product 1

HCID 178467194HCID 178467194, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in a similar manner as described above for Example 585 from (2S,4R)-1-[2-(3-acetyl-6-hydroxy-indol-1-yl)-acetyl]-4-fluoro-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide Example 583 (60.0 mg, 0.122 mmol), cesium carbonate (120 mg, 0.367 mmol) and 5-(chloromethyl)-1H-tetrazole (44.0 mg, 0.366 mmol) in DMSO (2.5 mL). Solid. MS (LC/MS): 572 [M+H]+; tR (HPLC conditions k): 3.23 min.

Workup

  1. custom3.23 min.

Sources & evidence

ORD record
ord-e9a90f63b5d0468d99e638fd9720fa32
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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