Dimethylformamide → HCID 86628225, compound

HRID 1821439Notes

Reaction equation

HRID 1821439 reaction equation
[CH3:1][C:2]1[C:3]2[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([OH:9])=O.S(Cl)(Cl)=O.C[N:19](C=O)C.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](/[CH:32]=[CH:33]/[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2N)=[N:24]1.C(N(CC)CC)C>C1COCC1.ClCCl>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](/[CH:32]=[CH:33]/[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:13]2[C:3]3[C:2]([CH3:1])=[C:6]([C:7]([NH2:19])=[O:9])[S:5][C:4]=3[CH:10]=[CH:11][CH:12]=2)=[N:24]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 8218683-methylbenzo[b]thiophene-2-carboxylic acidHCID 69001756HCID 69001756, compound

Product 1

HCID 86628225HCID 86628225, compoundYield 490.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Example 29, 3-methylbenzo[b]thiophene-2-carboxylic acid (0.14 g, 0.70 mmol) was treated with thionyl chloride (79 μL, 1.1 mmol), DMF (7.4 μL, 0.13 mmol) and dichloromethane (3.0 mL), followed by reacting with Compound 2 (0.15 g, 0.64 mmol), triethylamine (0.23 mL, 1.6 mmol) and THF (3.0 mL) to obtain Compound 351 (261 mg, 100%).

Sources & evidence

ORD record
ord-15095a32acac4129b9399fa0bb2d9082
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…