1,2-Dichloroethane → Tert-butyl 2-{2-{(2-methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinoyl}hydrazinecarboxylate

HRID 1944580Notes

Reaction equation

HRID 1944580 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:21][C@@H:22]1[CH2:24][C@H:23]1[CH3:25])[C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N:15]([CH3:20])[S:16]([CH3:19])(=[O:18])=[O:17])[N:14]=1)[C:9](O)=[O:10].C(N(C(C)C)CC)(C)C.[C:35]([NH:42][NH2:43])([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:21][C@@H:22]1[CH2:24][C@H:23]1[CH3:25])[C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N:15]([CH3:20])[S:16]([CH3:19])(=[O:17])=[O:18])[N:14]=1)[C:9]([NH:43][NH:42][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:10]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 694982882-{(2-Methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinic acid

Product 1

HCID 69498271Tert-butyl 2-{2-{(2-methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinoyl}hydrazinecarboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-{(2-methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinic acid (14.05 g, 37.8 mmol) in DCM (150 mL) was added diisopropylethyl amine (7.91 mL, 45.4 mmol), Boc-hydrazine (6 g, 45.4 mmol), HOAt (1.03 g, 7.6 mmol) and EDC (8.7 g, 45.4 mmol), and the reaction mixture was stirred at rt for 16 h. The reaction mixture was diluted with EtOAc, washed with 10% KHSO4, aq NaHCO3 and brine, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography (silica, 30% to 70% EtOAc in hexane) to give tert-butyl 2-{2-{(2-methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinoyl}hydrazinecarboxylate. MS M+1=486.

Workup

  1. washwashed with 10% KHSO4, aq NaHCO3 and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (silica, 30% to 70% EtOAc in hexane)

Sources & evidence

ORD record
ord-6a78eba3df9c45099717f403c5b47735
Source dataset
uspto-grants-2013_03
Patent number
US08394837B2

Reaction notes

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