Diisopropylethylamine → Tert-butyl 3-[(4-amino-5-cyano-1,3-thiazol-2-yl)amino]piperidine-1-carboxylate

HRID 444846Notes

Reaction equation

HRID 444846 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](S(C)(=O)=O)[S:5][C:6]=1[C:7]#[N:8].[NH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C.O>[NH2:1][C:2]1[N:3]=[C:4]([NH:13][CH:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)[S:5][C:6]=1[C:7]#[N:8]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 5458091-BOC-3-AminopiperidineHCID 198350775-Thiazolecarbonitrile, 4-amino-2-(methylsulfonyl)-

Product 1

HCID 57911784Tert-butyl 3-[(4-amino-5-cyano-1,3-thiazol-2-yl)amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

643 mg (3.17 mmol) of 4-amino-2-(methylsulfonyl)-1,3-thiazole-5-carbonitrile (Example 6A) were dissolved in 16 ml of DMSO, and 500 mg (2.11 mmol) of tert-butyl 3-aminopiperidine-1-carboxylate and 3.49 ml (21.12 mmol) of N,N-diisopropylethylamine were added. The mixture was heated in a microwave at 120° C. for 45 min. The reaction mixture was taken up in a mixture of ethyl acetate and water. The organic phase was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated on a rotary evaporator. The crude product was used without further purification.

Workup

  1. washThe organic phase was washed with saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated on a rotary evaporator
  4. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-67a821d5a0494b62bc9bbd9a9f4268d6
Source dataset
uspto-grants-2013_07
Patent number
US08476267B2

Reaction notes

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