Dimethylformamide → HCID 89382117, compound

HRID 1050513Notes

Reaction equation

HRID 1050513 reaction equation
[CH:1]1([N:4]([CH3:11])[CH2:5]/[CH:6]=[CH:7]/[C:8](O)=[O:9])[CH2:3][CH2:2]1.CN(C=O)C.C(Cl)(=O)C([Cl:20])=O>C(Cl)Cl>[CH:1]1([N:4]([CH3:11])[CH2:5]/[CH:6]=[CH:7]/[C:8]([Cl:20])=[O:9])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 62344125HCID 62344125, compound

Product 1

HCID 89382117HCID 89382117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-4-(cyclopropyl(methyl)amino)but-2-enoic acid (2.00 g, 12.9 mmol) in DCM (60 mL) was added DMF (0.2 mL) and oxalyl chloride (4.42 mL, 51.6 mmol). The mixture was stirred at RT for 4 h and concentrated in vacuo to dryness to afford (E)-4-(cyclopropyl(methyl)amino)but-2-enoyl chloride. In a similar manner as described in Example 70, (R,E)-3-(1-(4-(cyclopropyl(methyl)amino)but-2-enoyl)pyrrolidin-3-ylamino)-5-(4-(morpholine-4-carbonyl)phenylamino)-1,2,4-triazine-6-carboxamide (85) was prepared using (E)-4-(cyclopropyl(methyl)amino)but-2-enoyl chloride. MS found for C27H35N9O4 as (M+H)+ 550.2, (M−H)− 548.3. UV: λ=248 nm.

Workup

  1. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-866383d367d447c799da92d011b60924
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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