Pyridine → tert-Butyl 2-[3-chloro-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]pyrazolidine-1-carboxylate

HRID 225433

Reaction equation

HRID 225433 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C:9]2=[O:14])=[C:4]([Cl:15])[CH:3]=1.Cl[C:17](OC1C=CC([N+]([O-])=O)=CC=1)=[O:18].N1C=CC=CC=1.[N:35]1([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39][CH2:38][CH2:37][NH:36]1.C(N(C(C)C)C(C)C)C>ClCCl>[Cl:15][C:4]1[CH:3]=[C:2]([NH:1][C:17]([N:36]2[CH2:37][CH2:38][CH2:39][N:35]2[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:18])[CH:7]=[CH:6][C:5]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][C:9]1=[O:14]

Participants

7

Reactant 5

HCID 1049PyridineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 21857793tert-Butyl pyrazolidine-1-carboxylateHCID 231053274-(4-Amino-2-chlorophenyl)morpholin-3-one

Product 1

HCID 86607077tert-Butyl 2-[3-chloro-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]pyrazolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

340 mg (1.5 mmol) of 4-(4-amino-2-chlorophenyl)morpholin-3-one are dissolved in 10 ml of dichloromethane (DCM), 302 mg (1.5 mmol) of 4-nitrophenyl chloroformate and 121 μl (1.5 mmol) of pyridine are subsequently added successively, and the mixture is stirred at RT for 1 h. 300.0 mg (0.7 mmol) of tert-butyl pyrazolidine-1-carboxylate and 0.765 mg (4.5 mmol) of N-ethyldiisopropylamine are added to this reaction mixture. After stirring at RT for 20 h, the mixture is subjected to conventional work-up, giving 420 mg (57.3%) of step 1; MS (FAB) m/e=425/427 (M+H)+.

Workup

  1. stirringAfter stirring at RT for 20 h
  2. customgiving 420 mg (57.3%) of step 1

Sources & evidence

ORD record
ord-205a888a3d854f2a95982cedf6ba42b4
Source dataset
uspto-grants-2009_07
Patent number
US07557102B2

Linked notes

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