Dicyclohexylcarbodiimide → HCID 67248269, compound

HRID 2425032Notes

Reaction equation

C1CCC(N=C=NC2CCCCC2)CC1.[CH3:16][C:17]1[O:21][N:20]=[C:19]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[C:27](=[O:31])[N:26]([CH2:32][C:33]([OH:35])=O)[CH2:25]3)[N:18]=1.ON1C2C=CC=CC=2N=N1.[CH2:46]([O:48][C:49](=[O:57])[CH2:50][N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)[CH3:47]>CN(C=O)C>[CH2:46]([O:48][C:49](=[O:57])[CH2:50][N:51]1[CH2:56][CH2:55][N:54]([C:33](=[O:35])[CH2:32][N:26]2[CH2:25][C:24]3[C:28](=[CH:29][CH:30]=[C:22]([C:19]4[N:18]=[C:17]([CH3:16])[O:21][N:20]=4)[CH:23]=3)[C:27]2=[O:31])[CH2:53][CH2:52]1)[CH3:47]

Participants

Conditions

Temperature: 0 °C

Procedure

DCC (0.433 g; 2.1 mmol) was added with vigorous stirring to a solution of the compound of example 66d (0.53 g; 1.9 mmol) and 1-hydroxybenzotriazole (0.338 g; 2.47 mmol) in dry DMF (15 ml) at 0° C. After 10 min. piperazin-1-yl-acetic acid ethyl ester (0.43 g; 2.47 mmol) was added to the mixture It was stirred at 0° C. for 1 h and then kept in the freezer over night. The DCU was filtered off and the filtrate was washed with 1N aqueous NaHCO3, water, 1N aqueous HCl, brine, dried (Na2SO4), concentrated and purified using flash chromatography (silica gel, 5% MeOH in chloroform) to obtain the title compound. Yield, 0.64 g (77%); mp, 189-90° C.; MS (ESI+): 450 (M++Na), analysis: C21H25N5O5 requires C, 59.01; H, 5.90; N, 16.38; found: C, 58.80; H, 5.93; N, 15.80%.

Workup

waitkept in the freezer over night
filtrationThe DCU was filtered off
washthe filtrate was washed with 1N aqueous NaHCO3, water, 1N aqueous HCl, brine
dry with materialdried (Na2SO4)
concentrationconcentrated
custompurified

Sources & evidence

ORD record: ord-2347f0b5ba684bdf87d703a27a054fdb
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964628B2

Reaction notes

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