Diisopropylethylamine → 4-[(2-Chloro-pyrimidine-5-carbonyl)-cyclopropyl-amino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1409689Notes

Reaction equation

HRID 1409689 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][N:3]=1.C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.ClC(N(C)C)=[N+](C)C.[C:35]([O:39][C:40]([N:42]1[CH2:47][CH2:46][CH:45]([NH:48][CH:49]2[CH2:51][CH2:50]2)[CH2:44][CH2:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36]>O1CCCC1>[C:35]([O:39][C:40]([N:42]1[CH2:47][CH2:46][CH:45]([N:48]([C:8]([C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[N:3][CH:4]=2)=[O:10])[CH:49]2[CH2:50][CH2:51]2)[CH2:44][CH2:43]1)=[O:41])([CH3:38])([CH3:36])[CH3:37]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2769591tert-Butyl 4-(cyclopropylamino)piperidine-1-carboxylateHCID 10989639Chloro-N,N,N',N'-tetramethylformamidinium HexafluorophosphateHCID 110949062-Chloropyrimidine-5-carboxylic acid

Product 1

HCID 866861524-[(2-Chloro-pyrimidine-5-carbonyl)-cyclopropyl-amino]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-chloropyrimidine-5-carboxylic acid (2.00 g), ethyldiisopropylamine (6.39 mL), and chloro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (4.21 g) in tetrahydrofuran (15 mL) is stirred for 45 min at room temperature prior to the addition of 4-cyclopropylamino-piperidine-1-carboxylic acid tert-butyl ester (2.94 g). The resulting mixture is stirred at room temperature for 1 h. The solvent is evaporated in vacuo and the residue purified by HPLC(H2O/MeOH/TFA). LC (method 3): tR=1.89 min; Mass spectrum (ESI+): m/z=381/383 (Cl) [M+H]+.

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 1 h
  2. customThe solvent is evaporated in vacuo
  3. customthe residue purified by HPLC(H2O/MeOH/TFA)

Sources & evidence

ORD record
ord-4dbd7ef2b1a04bbb8fe2a513fb343481
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

Loading…