Ethyl Acetate → HCID 66832997, compound

HRID 2044075Notes

Reaction equation

Cl[C:2]1[CH:10]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[CH:14][CH:13]=2)[C:5]([C:6]([NH2:8])=[O:7])=[C:4]([O:26][CH2:27][CH2:28][CH3:29])[N:3]=1.[NH:30]1[CH2:35][CH2:34][CH2:33][C@@H:32]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:31]1.C(OCC)(=O)C>C1COCC1>[C:6]([C:5]1[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[CH:14][CH:13]=2)=[CH:10][C:2]([N:30]2[CH2:35][CH2:34][CH2:33][C@@H:32]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:40])[CH3:42])[CH2:31]2)=[N:3][C:4]=1[O:26][CH2:27][CH2:28][CH3:29])(=[O:7])[NH2:8]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-chloro-4-(4-(morpholine-4-carbonyl)phenylamino)-2-propoxynicotinamide (500 mg, 1.194 mmol) and (R)-tert-butyl piperidin-3-ylcarbamate (956 mg, 4.77 mmol) in THF (3 mL) was sealed in a vial and heated at 100° C. for 24 hrs. The reaction mixture was dissolved into ethyl acetate, washed with water, and concentrated. The solid material was chromatographed on an ISCO Companion 40 g silica gel column and eluted with (90:9:1 CH2Cl2:MeOH:NH4OH)/CH2Cl2 gradient (10-100%) to give 530 mg of (R)-tert-butyl 1-(5-carbamoyl-4-(4-(morpholine-4-carbonyl)phenylamino)-6-propoxypyridin-2-yl)piperidin-3-ylcarbamate as a white solid. LCMS: (M+H)+=583.46.

Workup

customwas sealed in a vial and
washwashed with water
concentrationconcentrated
customThe solid material was chromatographed on an ISCO Companion 40 g silica gel column
washeluted with (90:9:1 CH2Cl2:MeOH:NH4OH)/CH2Cl2 gradient (10-100%)

Sources & evidence

ORD record: ord-f845dbfd5bda4cd2a8770fab79206ef8
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586751B2

Reaction notes

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