Tetrahydrofuran → HCID 57505711, compound

HRID 1663978Notes

Reaction equation

HRID 1663978 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=O.C(Cl)(=O)C(Cl)=O.O1CCCC1.[NH2:27][C:28]1[CH:29]=[C:30]([CH:47]=[CH:48][CH:49]=1)[O:31][C:32]1[CH:33]=[CH:34][C:35]2[N:36]([CH:38]=[C:39]([NH:41][C:42]([CH:44]3[CH2:46][CH2:45]3)=[O:43])[N:40]=2)[N:37]=1>CN(C)C=O.CN1CCCC1=O>[CH:44]1([C:42]([NH:41][C:39]2[N:40]=[C:35]3[CH:34]=[CH:33][C:32]([O:31][C:30]4[CH:29]=[C:28]([NH:27][C:10](=[O:12])[C:9]5[CH:13]=[CH:14][CH:15]=[C:7]([N:3]6[CH2:4][CH2:5][CH2:6][C:2]6=[O:1])[CH:8]=5)[CH:49]=[CH:48][CH:47]=4)=[N:37][N:36]3[CH:38]=2)=[O:43])[CH2:45][CH2:46]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 32407943-(2-oxopyrrolidin-1-yl)benzoic acidHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505711HCID 57505711, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using 3-(2-oxopyrrolidin-1-yl)benzoic acid (120 mg, 0.58 mmol), oxalyl chloride (60 μL, 0.68 mmol), N,N-dimethylformamide (1 drop), tetrahydrofuran (3.0 mL), N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (150 mg, 0.49 mmol) and N-methylpyrrolidone (2.0 mL) as starting materials and in the same manner as in Example 335, the title compound (170 mg, 70%) was obtained as a white powder.

Sources & evidence

ORD record
ord-e321c7ca4d814c9ea70d18c9c45086da
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

Loading…