Triethylamine → 2-(3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureido)acetamide

HRID 1626576Notes

Reaction equation

HRID 1626576 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:6][CH:5]=1)=[C:2]=[O:3].Cl.[NH2:20][CH2:21][C:22]([NH2:24])=[O:23].C(N(CC)CC)C>C1COCC1>[CH3:17][C:12]1([CH3:18])[C:13]([CH3:16])([CH3:15])[O:14][B:10]([C:7]2[CH:8]=[CH:9][C:4]([NH:1][C:2](=[O:3])[NH:20][CH2:21][C:22]([NH2:24])=[O:23])=[CH:5][CH:6]=2)[O:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723639Glycinamide hydrochlorideHCID 27734742-(4-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 666870852-(3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureido)acetamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (300 mg, 1.22 mmol) was dissolved in dry THF and stirred with 2-aminoacetamide hydrochloride (108 mg, 1.46 mmol) and triethylamine (drops) at 60° C. overnight. The mixture was reduced in vacuo, yielding the title compound (345 mg, 1.08 mmol, 88%).

Sources & evidence

ORD record
ord-bbda3ac0fcd04cd0a7d8327cb774b4fc
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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