Diisopropylethylamine → HCID 178462143, compound

HRID 1968311Notes

Reaction equation

HRID 1968311 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]([NH:18][C@H:19]([C:21]([OH:23])=[O:22])[CH3:20])=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1)=[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.FC(F)(F)C(O)=O.N[C@H](C(O[CH2:69][CH2:70][O:71][C:72]1[CH:77]=[CH:76][C:75]([C:78]2[C:83]([C:84]#[N:85])=[C:82]([N:86]3[CH2:90][CH2:89][CH2:88][CH2:87]3)[N:81]=[C:80]([S:91][CH2:92][C:93]3[N:94]=[C:95]([C:98]4[CH:103]=[CH:102][C:101]([Cl:104])=[CH:100][CH:99]=4)[S:96][CH:97]=3)[C:79]=2[C:105]#[N:106])=[CH:74][CH:73]=1)=O)C>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]([NH:18][C@H:19]([C:21]([O:23][CH2:69][CH2:70][O:71][C:72]1[CH:73]=[CH:74][C:75]([C:78]2[C:83]([C:84]#[N:85])=[C:82]([N:86]3[CH2:87][CH2:88][CH2:89][CH2:90]3)[N:81]=[C:80]([S:91][CH2:92][C:93]3[N:94]=[C:95]([C:98]4[CH:99]=[CH:100][C:101]([Cl:104])=[CH:102][CH:103]=4)[S:96][CH:97]=3)[C:79]=2[C:105]#[N:106])=[CH:76][CH:77]=1)=[O:22])[CH3:20])=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 687647022-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl L-alaninate trifluoroacetateHCID 178462142HCID 178462142, compound

Product 1

HCID 178462143HCID 178462143, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

257 mg (0.724 mmol) of N-(tert-butoxycarbonyl)-L-histidyl-L-alanine together with 151 mg (0.790 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 151 mg (0.988 mmol) of 1-hydroxy-1H-benzotriazole hydrate and 0.574 ml (3.293 mmol) of N,N-diisopropylethylamine were dissolved in 10 ml of DMF, after which 500 mg (0.659 mmol) of 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 L-alaninate trifluoroacetate were added. The reaction mixture was stirred at room temperature overnight and then purified twice by preparative HPLC (acetonitrile/water). This gave 169 mg (28% of theory) of the target compound.

Workup

  1. custompurified twice by preparative HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-bb0cb0c346434e7db7634685301a4edc
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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