Methylamine → 4-{[({[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}amino)carbonyl]amino}-N-methylbutanamide

HRID 1371458Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:6][N:7]1[CH2:12][CH2:11][O:10][C@@H:9]([CH2:13][NH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)=[O:16])[CH2:8]1.[CH3:28][NH2:29]>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:6][N:7]1[CH2:12][CH2:11][O:10][C@@H:9]([CH2:13][NH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]([NH:29][CH3:28])=[O:23])=[O:16])[CH2:8]1

Participants

Conditions

Temperature: 22 °C

Procedure

N,N′-carbonyldiimidazole (0.0132 g) was added to a stirred solution of Intermediate 26 (0.030 g) in N,N-dimethylformamide (2 ml), and the mixture stirred at 22° C. under nitrogen for 40 min. Methylamine (2.0M solution in tetrahydrofuran, 0.102 ml) was added, and stirring was continued at 22° C. for 17 h. The mixture was applied directly to a sulphonic acid ion exchange cartridge (2 g Isolute SCX), and eluted with methanol followed by 10% 0.880 ammonia in methanol to give a gum (0.042 g). Purification by chromatography on silica gel (1 g Varian Bond Elut cartridge), eluting with chloroform, ether, ethyl acetate, acetone, and methanol, gave a gum (0.025 g), which was further purified by mass directed preparative HPLC to give the title compound as a colourless gum (7.2 mg).

Workup

stirringstirring
waitwas continued at 22° C. for 17 h
washeluted with methanol

Sources & evidence

ORD record: ord-5743046291514f7f994c7a7d2ac60822
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157457B2

Reaction notes

Loading…