Hydrazine hydrate (1:1) → Tert-butyl 3-[4-[5-amino-6-(hydrazinecarbonyl)pyrazin-2-yl]phenyl]sulfonylpiperidine-1-carboxylate

HRID 78723Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:30]([O:32]C)=O)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.O.[NH2:35][NH2:36]>O1CCOCC1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:18]3)(=[O:15])=[O:16])=[CH:10][CH:9]=2)=[N:4][C:3]=1[C:30]([NH:35][NH2:36])=[O:32]

Participants

Conditions

Temperature: 65 °C

Procedure

methyl 3-amino-6-[4-[(1-tert-butoxycarbonyl-3-piperidyl)sulfonyl]phenyl]pyrazine-2-carboxylate (1.65 g, 3.462 mmol) in dioxane (16.50 mL) was treated with hydrazine hydrate (866.5 mg, 842.1 μL, 17.31 mmol) and stirred at 65° C. for 2.5 hours. The reaction mixture was concentrated in vacuo. The residue was treated with water and stirred for 1 hour, filtered and washed with water, and dried overnight under high vacuum giving tert-butyl 3-[4-[5-amino-6-(hydrazinecarbonyl)pyrazin-2-yl]phenyl]sulfonylpiperidine-1-carboxylate (1.572 g, 3.272 mmol, 93.77%) as a pale yellow powder. LC/MS m/z 421.1 [M−56+1]+.

Workup

concentrationThe reaction mixture was concentrated in vacuo
additionThe residue was treated with water
stirringstirred for 1 hour
filtrationfiltered
washwashed with water
customdried overnight under high vacuum

Sources & evidence

ORD record: ord-ebe748d6a9454aa2917106bcb4467225
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841449B2

Reaction notes

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