Triethylamine → HCID 178490666, compound

HRID 538767Notes

Reaction equation

HRID 538767 reaction equation
[C:1]([C:5]1[S:9][C:8](=[NH:10])[N:7]([CH2:11][C:12]2([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([O:29][CH3:30])=[C:24]([CH:28]=1)[C:25](O)=[O:26].S(Cl)(Cl)=O.C(N(CC)CC)C>C1COCC1>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:25](=[O:26])[C:24]2[CH:28]=[C:20]([Cl:19])[CH:21]=[CH:22][C:23]=2[O:29][CH3:30])/[N:7]([CH2:11][C:12]2([OH:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 769705-Chloro-o-anisic acidHCID 668518251-((5-tert-butyl-2-iminothiazol-3(2H)-yl)methyl)cyclohexanol

Product 1

HCID 178490666HCID 178490666, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 20A (1.3 g, 3.7 mmol), 5-chloro-2-methoxybenzoic acid (0.70 g, 3.7 mmol), thionyl chloride (10 mL) and triethylamine (1.6 mL, 11 mmol) in THF (25 mL) were processed as described in Example 18B and Example 18C to provide the title compound (0.82 g, 1.9 mmol, 50% yield). MS (DCI/NH3) m/z 437 (M+H)+.

Sources & evidence

ORD record
ord-bc86c57bfb884960b63482333b2510f6
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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