2,5-dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]thiophene-3-carboxylic acid → methyl 4-{(1S)-1-[({2,5-dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]-3-thienyl}carbonyl)amino]ethyl}benzoate

HRID 870050Notes

Reaction equation

HRID 870050 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:25])=[C:5]([CH:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[C:6]=1[C:7](O)=[O:8].[Cl-].[CH3:27][O:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([C@@H:37]([NH3+:39])[CH3:38])=[CH:33][CH:32]=1)=[O:30]>>[Cl:1][C:2]1[S:3][C:4]([Cl:25])=[C:5]([CH:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[C:6]=1[C:7]([NH:39][C@H:37]([C:34]1[CH:35]=[CH:36][C:31]([C:29]([O:28][CH3:27])=[O:30])=[CH:32][CH:33]=1)[CH3:38])=[O:8]

Participants

3

Reactant 2

HCID 579009752,5-dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]thiophene-3-carboxylic acidHCID 161770108[(1S)-1-(4-methoxycarbonylphenyl)ethyl]azanium chloride

Product 1

HCID 57900986methyl 4-{(1S)-1-[({2,5-dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]-3-thienyl}carbonyl)amino]ethyl}benzoate

Procedure

2,5-Dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]thiophene-3-carboxylic acid from Example 8, Step 3 (207 mg, 0.491 mmol) was reacted with (1S)-1-[4-(methoxycarbonyl)phenyl]ethanaminium chloride from Example 1, Step 9 under conditions similar to Example 1, Step 10. The crude product was purified by Combi Flash chromatography system (2-8% EtOAc/toluene in 20 min.) to afford the desired product as a white foam.

Workup

  1. customThe crude product was purified by Combi Flash chromatography system (2-8% EtOAc/toluene in 20 min.)

Sources & evidence

ORD record
ord-57c2aaec7e854359a99c2aac67c49789
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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