Triethylamine → HCID 178490666, compound

HRID 254626Notes

Reaction equation

HRID 254626 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-ec2b8adfa7e344f6ac99834959cb9697
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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