tert-Butyl carbazate → HCID 58169261, compound

HRID 1484977Notes

Reaction equation

HRID 1484977 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([C:9]2[S:13][C:12]([S:14](Cl)(=[O:16])=[O:15])=[CH:11][CH:10]=2)[N:3]=1.[NH:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH2:19].CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([C:9]2[S:13][C:12]([S:14]([NH:19][NH:18][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])(=[O:16])=[O:15])=[CH:11][CH:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 58169432HCID 58169432, compound

Product 1

HCID 58169261HCID 58169261, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(4-bromo-5-chloropyrimidin-2-yl)thiophene-2-sulfonyl chloride (164 mg, 0.45 mmol, 1.0 equiv.), tert-butyl hydrazinecarboxylate (119 mg, 0.9 mmol, 2.0 equiv.) and DIPEA (5 mL) was stirred in DCM at r.t. for 2 h, The reaction was extracted with EA and the combined layers were dried (Na2SO4), filtered. The filtrate was concentrated to afford tert-butyl 2-(5-(4-bromo-5-chloropyrimidin-2-yl)thiophen-2-ylsulfonyl)hydrazinecarboxylate (179 mg, 85%). LC-MS (m/z)=469 [M+H]+

Workup

  1. extractionThe reaction was extracted with EA
  2. dry with materialthe combined layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7b9624d2b232475cbe22e2649c4904b8
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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