Dimethylformamide → HCID 69000935, compound

HRID 1821442Notes

Reaction equation

HRID 1821442 reaction equation
[CH3:1][S:2]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].S(Cl)(Cl)=O.CN(C=O)C.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](/[CH:31]=[CH:32]/[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[NH2:39])=[N:23]1.C(N(CC)CC)C>C1COCC1.ClCCl>[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](/[CH:31]=[CH:32]/[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[NH:39][C:10]([C:8]2[S:9][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[O:12])=[N:23]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27404975-Methanesulfonylthiophene-2-carboxylic acidHCID 69001756HCID 69001756, compound

Product 1

HCID 69000935HCID 69000935, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Example 29, 5-(methylsulfonyl)thiophene-2-carboxylic acid (97 mg, 0.47 mmol) was treated with thionyl chloride (53 μL, 0.72 mmol), DMF (5.0 μL, 0.085 mmol) and dichloromethane (2.0 mL), followed by reacting with Compound 2 (0.10 g, 0.43 mmol), triethylamine (60 μL, 1.1 mmol) and THF (2.0 mL) to obtain Compound 354 (58 mg, 32%).

Sources & evidence

ORD record
ord-b300af0304a045c5a5e2ccfd46396860
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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