Dimethylamine → HCID 66829247, compound

HRID 1685755Notes

Reaction equation

[CH2:1]([C:3]1[CH:18]=[C:17]([C:19]2[O:20][C:21]([C:24]3[S:25][C:26]([CH:30]=O)=[C:27]([CH3:29])[CH:28]=3)=[N:22][N:23]=2)[CH:16]=[C:15]([CH3:32])[C:4]=1[O:5][CH2:6][C@@H:7]([OH:14])[CH2:8][NH:9][C:10](=[O:13])[CH2:11][OH:12])[CH3:2].[CH3:33][NH:34][CH3:35]>>[CH3:33][N:34]([CH2:30][C:26]1[S:25][C:24]([C:21]2[O:20][C:19]([C:17]3[CH:16]=[C:15]([CH3:32])[C:4]([O:5][CH2:6][C@@H:7]([OH:14])[CH2:8][NH:9][C:10](=[O:13])[CH2:11][OH:12])=[C:3]([CH2:1][CH3:2])[CH:18]=3)=[N:23][N:22]=2)=[CH:28][C:27]=1[CH3:29])[CH3:35]

Participants

Reactant 2

HCID 674Dimethylamine

HCID 86646453HCID 86646453, compound

Product 1

HCID 66829247HCID 66829247, compoundYield 31.5%

Procedure

The title compound (4 mg) is prepared starting from N-((2S)-3-{2-ethyl-4-[5-(5-formyl-4-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide (12 mg, 26 μmol) and dimethylamine (14 mg, 105 μmol) according to Method C; LC-MS*: tR=0.80 min; [M+1]+=488.95; 1H NMR (D6-DMSO): δ1.23 (t, J=7.5 Hz, 3H), 2.23 (s, 3H), 2.26 (s, 6H), 2.35 (s, 3H), 2.73 (q, J=7.5 Hz, 2H), 3.21-3.29 (m, 1H), 3.39-3.47 (m, 1H), 3.61 (s, 2H), 3.71-3.81 (m, 2H), 3.84 (d, J=3.3 Hz, 2H), 3.93-4.00 (m, 1H), 5.31 (d, J=5.3 Hz, 1H), 5.55 (t, J=5.5 Hz, 1H), 7.68-7.72 (m, 2H), 7.77 (s, 2H).

Sources & evidence

ORD record: ord-9dc016c39b85445195569f576cb6b66b
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148410B2

Reaction notes

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