Ethyl Acetate → HCID 15384374, compound

HRID 2258153Notes

Reaction equation

[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].Cl.[C:14]([C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:26][CH2:25][C@H:24]([NH2:27])[C:23]2=[O:28])=[CH:18][CH:17]=1)#[N:15].C(O)(=O)[C@@H](C1C=CC=CC=1)O.N[C@H](C)[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44].CCOC(C)=O>N1C=CC=CC=1.CN(C=O)C>[C:14]([C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH2:26][CH2:25][C@H:24]([NH:27][C:1]([NH:8][C@H:12]([CH3:11])[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])=[O:2])[C:23]2=[O:28])=[CH:20][CH:21]=1)#[N:15]

Participants

Conditions

Temperature: 5 °C

Procedure

To a suspension of 1,1'-carbonyldiimidazole (178 mg, 1.1 mmol) in pyridine (2.5 mL) at 5° C. under nitrogen was added the product of example 4 (260 mg, 1.1 mmol). The resulting solution was stirred at 5° C. for 15 minutes, diluted with 2.5 mL of DMF and removed from the ice bath. The product of example 8 (375 mg, 1.32 mmol) was added all at once and the reaction mixture stirred at 75°-80° C. for 2 hours. After cooling to room temperature, the resulting solution was diluted EtOAc and washed with 1N HCl, saturated NaHCO3 and dried (MgSO4). Evaporation of the solvent afforded 295 mg (73%) of product (m.p. 177.5°-179° C.). 1H-NMR (300 MHz, CDCl3) δ 1.20-1.30 (m, 6H), 2.05 (m, 1H), 2.53 (m, 2H), 2.83 (m, 1H), 3.83 (m, 2H), 4.15 (q, J=7Hz, 2H), 4.19 (m, 1H), 4.48 (m, 1H), 7.68 (d, J=8Hz, 2H), 7.82 (d, J=8Hz, 2H).

Workup

customremoved from the ice bath
stirringstirred at 75°-80° C. for 2 hours
temperatureAfter cooling to room temperature
washwashed with 1N HCl, saturated NaHCO3
dry with materialdried (MgSO4)
customEvaporation of the solvent

Sources & evidence

ORD record: ord-6954d3662043455581eede8824410107
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05659063

Reaction notes

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