Tetrahydro-4H-pyran-4-one → HCID 21906307, compound

HRID 988638Notes

Reaction equation

Cl.[C:2](N)(=[O:9])[C:3]1C=C[CH:6]=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([NH:35][C:36]([CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[O:37])=[C:23]([CH:34]=1)[C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=1)=[O:25].O1CCC(=O)CC1>>[ClH:18].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([NH:35][C:36]([CH:38]2[CH2:39][CH2:40][N:41]([CH:4]3[CH2:3][CH2:2][O:9][CH2:6][CH2:5]3)[CH2:42][CH2:43]2)=[O:37])=[C:23]([CH:34]=1)[C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=1)=[O:25]

Participants

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-one

HCID 12196675Benzamide, hydrochloride

HCID 21906226HCID 21906226, compound

Product 1

HCID 21906307HCID 21906307, compound

Procedure

Using methods substantially equivalent to those described in example 27, 5-chloro-N-(5-chloropyridin-2-yl)-2-[1-(tetrahydropyran-4-yl)piperidin-4-ylcarbonyl]amino]-benzamide hydrochloride (0.25 g, 56%) was prepared from 5-chloro-N-(5-chloropyridin-2-yl)-2-[(piperidin-4-ylcarbonyl)amino]benzamide trifluoroacetate and tetrahydro-4H-pyran-4-one. The preparative RPHPLC (C18) purification procedure was elution with a linear gradient of 90/10 to 50/50 (0.01% HCl/acetonitrile) over 180 min.

Workup

customThe preparative RPHPLC (C18) purification procedure
washelution with a linear gradient of 90/10 to 50/50 (0.01% HCl/acetonitrile) over 180 min.

Sources & evidence

ORD record: ord-4999ac9d36554ab491568ed89e68c2f5
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06635657B1

Reaction notes

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