Dimethylformamide → HCID 69000129, compound

HRID 1821440Notes

Reaction equation

HRID 1821440 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([OH:9])=O.S(Cl)(Cl)=O.CN(C=O)C.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH2:36])=[N:20]1.C(N(CC)CC)C>C1COCC1.ClCCl>[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][C:7]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=2)=[O:9])=[N:20]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 5576781-methyl-1H-imidazole-2-carboxylic acidHCID 69001756HCID 69001756, compound

Product 1

HCID 69000129HCID 69000129, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Example 29, 1-methyl-1H-imidazole-2-carboxylic acid (59 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 352 (50 mg, 34%).

Sources & evidence

ORD record
ord-9338c06d29a64095b39daff30b86a146
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…