Diisopropylcarbodiimide → 2(S)-{4-[3-(5-Chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenylcarbamoyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 2075760Notes

Reaction equation

HRID 2075760 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[C:14](=[O:40])[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:24]2[C:25]([C:32]3[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=3[OH:39])=[N:26][N:27]([CH2:29][CH2:30][OH:31])[CH:28]=2)=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NC1C=CC(C#CC2C(C3C=C(Cl)C=CC=3O)=NN(CCO)C=2)=CC=1.C(N1CCCC[C@@H]1C(O)=O)(OC(C)(C)C)=O.CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14](=[O:40])[NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]#[C:23][C:24]2[C:25]([C:32]3[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=3[OH:39])=[N:26][N:27]([CH2:29][CH2:30][OH:31])[CH:28]=2)=[CH:20][CH:21]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 688618(2R)-1-[(tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 135974913HCID 135974913, compoundHCID 135974981HCID 135974981, compound

Product 1

HCID 1359749312(S)-{4-[3-(5-Chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenylcarbamoyl}-piperidine-1-carboxylic acid tert-butyl esterYield 95.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Using the same procedure for the preparation of compound 4A, reaction of compound 2A (2.17 g, 6.13 mmol) and N-Boc-2(S)-piperidinecarboxylic acid (3A) (5.63 g, 24.55 mmol) in the presence of DMAP (0.30 g, 2.46 mmol) and (DIPC, 3.80 mL, 24.54 mmol) in anhydrous THF (40 mL) provided the title compound (9A, 3.30 g) as a foam-like powder in 95.2% yield. The 1H NMR and LCMS data are exactly same with those of compound 4A.

Sources & evidence

ORD record
ord-c10014ff579c41e2aeee973a0d47dd8e
Source dataset
uspto-grants-2011_04
Patent number
US07923004B2

Reaction notes

Loading…