Cesium carbonate → HCID 68283995, compound

HRID 1527571Notes

Reaction equation

HRID 1527571 reaction equation
[Cl:1][C:2]1[C:3]([F:41])=[C:4]([CH:38]=[CH:39][CH:40]=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:37])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][C:22]([O:26][CH2:27][C:28]3C=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:23][CH:24]=2)[C:19]([C:34](=[O:36])[CH3:35])=[CH:18]1)=[O:8].ClC1C(F)=C(C=CC=1)C[NH:47]C([C@@H]1C[C@@H](F)CN1C(=O)CN1C2C(=CC(O)=CC=2)C(C(=O)C)=C1)=O.C(=O)([O-])[O-].[Cs+].[Cs+].ClCC1N=CC=CN=1>CS(C)=O>[Cl:1][C:2]1[C:3]([F:41])=[C:4]([CH:38]=[CH:39][CH:40]=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:37])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][C:22]([O:26][CH2:27][C:28]3[N:47]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:23][CH:24]=2)[C:19]([C:34](=[O:36])[CH3:35])=[CH:18]1)=[O:8]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 128773712-(Chloromethyl)pyrimidineHCID 68283881HCID 68283881, compoundHCID 68284042HCID 68284042, compound

Product 1

HCID 68283995HCID 68283995, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared according to procedure described for the preparation of Example 589 (2S,4R)-1-{2-[3-acetyl-5-(pyridin-2-ylmethoxy)-indol-1-yl]-acetyl}-4-fluoro-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide from (2S,4R)-1-[2-(3-acetyl-5-hydroxy-indol-1-yl)-acetyl]-4-fluoro-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide Example 579 (23.0 mg, 0.047 mmol), cesium carbonate (61 mg, 0.188 mmol) and 2-(chloromethyl)pyrimidine (0.012 mg, 0.070 mmol) in DMSO (2 mL). White solid. MS (LC/MS): 582/583 [M+H]+; tR (HPLC conditions k): 3.19 min.

Workup

  1. custom3.19 min.

Sources & evidence

ORD record
ord-f9f2dc4f4e8b47d6afc1a10470106b0b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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