Diisopropylethylamine → HCID 86643857, compound

HRID 1968309Notes

Reaction equation

HRID 1968309 reaction equation
C1(N[CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)CCCCC1.[C:14]([O:18][C:19]([NH:21][C@@H:22]([CH2:26][CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:23]([OH:25])=O)=[O:20])([CH3:17])([CH3:16])[CH3:15].[ClH:36].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.[NH2:75][C@H:76]([C:78]([O:80][CH2:81][CH2:82][O:83][C:84]1[CH:89]=[CH:88][C:87]([C:90]2[C:95]([C:96]#[N:97])=[C:94]([N:98]3[CH2:102][CH2:101][CH2:100][CH2:99]3)[N:93]=[C:92]([S:103][CH2:104][C:105]3[N:106]=[C:107](C4C=CC(Cl)=CC=4)[S:108][CH:109]=3)[C:91]=2[C:117]#[N:118])=[CH:86][CH:85]=1)=[O:79])[CH3:77]>CN(C=O)C>[C:14]([O:18][C:19]([NH:21][C@@H:22]([CH2:26][CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:23]([NH:75][C@H:76]([C:78]([O:80][CH2:81][CH2:82][O:83][C:84]1[CH:89]=[CH:88][C:87]([C:90]2[C:95]([C:96]#[N:97])=[C:94]([N:98]3[CH2:99][CH2:100][CH2:101][CH2:102]3)[N:93]=[C:92]([S:103][CH2:104][C:105]3[N:106]=[C:107]([C:8]4[CH:9]=[CH:10][C:11]([Cl:36])=[CH:12][CH:13]=4)[S:108][CH:109]=3)[C:91]=2[C:117]#[N:118])=[CH:86][CH:85]=1)=[O:79])[CH3:77])=[O:25])=[O:20])([CH3:15])([CH3:16])[CH3:17]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 56777023Boc-Dab(Boc)-OH.DCHAHCID 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 trifluoroacetate

Product 1

HCID 86643857HCID 86643857, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

361 mg (0.724 mmol) of (2S)-2,4-bis((tert-butoxycarbonyl)amino)butanoic acid N,N-dicyclohexylamine salt 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 420 mg (67% of theory) of the target compound.

Workup

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

Sources & evidence

ORD record
ord-c8d04309f24d4957a84519f8bce86301
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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