Triethylamine → 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-N-methoxy-N-methyl-1,3-thiazole-5-carboxamide
Reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23]([OH:25])=O)=[CH:21][N:22]=2)[CH2:14][C@@H:13]1[F:26])=[O:10].CN([C:30]([O:34][N:35]1N=NC2C=CC=N[C:36]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.CNOC>CN(C=O)C.O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23]([N:35]([O:34][CH3:30])[CH3:36])=[O:25])=[CH:21][N:22]=2)[CH2:14][C@@H:13]1[F:26])=[O:10]Participants
7
Reactant 4
HCID 8471Triethylamine
HCID 14232N,O-Dimethylhydroxylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 117187292-[(3s,4r)-4-{[(3,4-Dichloro-5-Methyl-1h-Pyrrol-2-Yl)carbonyl]amino}-3-Fluoropiperidin-1-Yl]-1,3-Thiazole-5-Carboxylic AcidProduct 1
Reagents, catalysts & solvents 2
Procedure
2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-1,3-thiazole-5-carboxylic acid (10 mg, 0.024 mmol) was dissolved in dry DMF (10 ml), HATU (9.1 mg, 0.024 mmol), triethylamine (7.27 mg, 0.072 mmol) and N,O-dimethylhydroxyamine (4.65 mg, 0.048 mmol) were added. The mixture was stirred at room temperature for 30 minutes, then was poured into cold water (30 ml), the precipitate was filtered, washed with water and collected as the desired product (off white solid, 10 mg).
Workup
- filtrationthe precipitate was filtered
- washwashed with water
- customcollected as the desired product (off white solid, 10 mg)
Sources & evidence
- ORD record
- ord-bb685cfcf02242d89fe682c97a266295
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399489B2
Reaction notes
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