Diisopropylethylamine → 2-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-alaninate

HRID 1968305Notes

Reaction equation

HRID 1968305 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]2[S:54][CH:55]=[C:56]([CH2:58][S:59][C:60]3[C:65]([C:66]#[N:67])=[C:64]([C:68]4[CH:73]=[CH:72][C:71]([O:74][CH2:75][CH2:76]O)=[CH:70][CH:69]=4)[C:63]([C:78]#[N:79])=[C:62]([N:80]4[CH2:84][CH2:83][CH2:82][CH2:81]4)[N:61]=3)[N:57]=2)=[CH:49][CH:48]=1>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([O:13][CH2:76][CH2:75][O:74][C:71]1[CH:70]=[CH:69][C:68]([C:64]2[C:63]([C:78]#[N:79])=[C:62]([N:80]3[CH2:81][CH2:82][CH2:83][CH2:84]3)[N:61]=[C:60]([S:59][CH2:58][C:56]3[N:57]=[C:53]([C:50]4[CH:49]=[CH:48][C:47]([Cl:46])=[CH:52][CH:51]=4)[S:54][CH:55]=3)[C:65]=2[C:66]#[N:67])=[CH:73][CH:72]=1)=[O:12])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 46847262Neladenoson

Product 1

HCID 687678072-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-alaninate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

218 mg (1.15 mmol) of N-(tert-butoxycarbonyl)-L-alanine were initially charged in 5 ml of DMF. 240 mg (1.254 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 240 mg (1.568 mmol) of 1-hydroxy-1H-benzotriazole hydrate and 0.455 ml (2.613 mmol) of N,N-diisopropylethylamine were added, 300 mg (0.523 mmol) of 2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)-6-(pyrrolidin-1-yl)pyridine-3,5-dicarbonitrile (Example 1) were then added and the mixture was stirred at RT overnight. The reaction mixture was purified by preparative HPLC (acetonitrile/water+0.1% TFA). This gave 382 mg (98% of theory) of the target compound.

Workup

  1. customThe reaction mixture was purified by preparative HPLC (acetonitrile/water+0.1% TFA)

Sources & evidence

ORD record
ord-30d451b01c7842c0a7395d2414631a47
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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