Triethylamine → HCID 131728683, compound

HRID 1363391Notes

Reaction equation

HRID 1363391 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[O:14][C:15]2[C:20]([C:21](=[O:23])[CH:22]=1)=[C:19]([O:24][CH3:25])[CH:18]=[C:17]([O:26][CH3:27])[C:16]=2[C@@H:28]1[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][CH3:36])[CH2:30][C@H:29]1[OH:37].C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[O:14][C:15]2[C:20]([C:21](=[O:23])[CH:22]=1)=[C:19]([O:24][CH3:25])[CH:18]=[C:17]([O:26][CH3:27])[C:16]=2[C@@H:28]1[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][CH3:36])[CH2:30][C@H:29]1[O:37][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131728682HCID 131728682, compound

Product 1

HCID 131728683HCID 131728683, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methanesulfonyl chloride (0.178 g, 1.55 mmol), compound of example 129 (0.55 g, 1.2 mmol) and triethylamine (1 mL) in CHCl3 (10 mL), were reacted as described in example 3, method A to obtain (±)-trans-methanesulfonic acid 4-[2-(2-chloro-phenyl)-5,7-dimethoxy-4-oxo-4H-chromen-8-yl]-1-propyl-piperidin-3-yl ester. This was dissolved in dry IPA at 80-90° C., anhydrous NaOAc (0.49 g, 5.98 mmol) was added, and the reaction mixture was processed as in example 3, method A to give an oily residue which was purified using a silica gel column and 1% IPA+1% liquor NH3 in CHCl3 as eluant to obtain the title compound.

Sources & evidence

ORD record
ord-0c3973aa542e4961b259885827e5df03
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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