Ethyl Acetate → HCID 59367625, compound

HRID 2079821Notes

Reaction equation

[CH2:1]1[CH:5]2[CH2:6][NH:7][CH2:8][CH:4]2[CH2:3][N:2]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].Cl[C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:18]=1.CCN(C(C)C)C(C)C.CCOC(C)=O>O1CCOCC1>[C:12]([O:11][C:9]([N:2]1[CH2:3][CH:4]2[CH2:8][N:7]([C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:18]=3)[CH2:6][CH:5]2[CH2:1]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of tert-butyl hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylate (1.11 g, 5.23 mmol) in dioxane were added ethyl 6-chloronicotinate (1.28 g, 6.9 mmol) and DIPEA (2 ml, 11.6 mmol). The mixture was heated at 75° C. for 3 days. The mixture was then poured into EtOAc (100 ml) and washed with saturated ammonium chloride (50 ml), water (50 ml) and brine (50 ml). The organic fraction was dried (MgSO4), concentrated and purified by flash column chromatography (5% MeOH-DCM) to yield the title compound (1.429 g, 75%). m/z 362.25 [M+H]+; 1H NMR (300 MHz, CDCl3) δ: 8.32 (1H, dd, J=0.6, 2.1 Hz), 8.03 (1H, dd, J=2.4, 9.0 Hz), 6.32 (1H, d, J=8.7 Hz), 4.34 (2H, q, J=6.9 Hz), 3.24-3.85 (8H, m), 3.03 (2H, m), 1.47 (9H, s), 1.38 (3H, t, J=7.2 Hz).

Workup

washwashed with saturated ammonium chloride (50 ml), water (50 ml) and brine (50 ml)
dry with materialThe organic fraction was dried (MgSO4)
concentrationconcentrated
custompurified by flash column chromatography (5% MeOH-DCM)

Sources & evidence

ORD record: ord-09450e60a3494c8c9e51017ba855dd60
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932246B2

Reaction notes

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