Pyridine → methyl 4-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}amino)-1H-indazole-1-carboxylate

HRID 451600Notes

Reaction equation

[C:1](=[O:4])([OH:3])[NH2:2].N[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][N:7]=1.[CH2:15]1[C:20](=[O:21])[N:19]([O:22][C:23](ON2C(=O)CCC2=O)=[O:24])[C:17](=[O:18])[CH2:16]1.N1C=CC=C[CH:34]=1>C(#N)C>[CH3:34][O:4][C:1]([N:2]1[C:13]2[C:14](=[C:9]([NH:8][C:23]([O:22][N:19]3[C:20](=[O:21])[CH2:15][CH2:16][C:17]3=[O:18])=[O:24])[CH:10]=[CH:11][CH:12]=2)[CH:6]=[N:7]1)=[O:3]

Participants

Conditions

Temperature: 40 °C

Procedure

To a 3-necked 2-L flask fitted with a mechanical stirrer and a nitrogen inlet were charged the aminoindazole carbamate (94.5 g, 1.0 equiv.), N,N′-disuccinimidyl carbonate (113.8 g, 1.07 eq), and dry acetonitrile (950 mL, KF=0.06%). Pyridine (32.8 g, 1.0 eq) was added to the mixture and it was heated to 40° C. and stirred for 15 h during which time a solid precipitated. The solid was filtered, washed with fresh dry acetonitrile (3×100 mL), and dried in a vacuum oven at 40° C. to afford 130.1 g (92.9% potency adjusted) of the activated succinimidyl carbamate as a light brown solid.

Workup

customTo a 3-necked 2-L flask fitted with a mechanical stirrer and a nitrogen inlet
customprecipitated
filtrationThe solid was filtered
washwashed with fresh dry acetonitrile (3×100 mL)
customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record: ord-a0156b1aa4ce4231b77eb62998b38eee
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487116B2

Reaction notes

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