4-Methylmorpholine → HCID 9821989, compound

HRID 987223Notes

Reaction equation

HRID 987223 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]([OH:14])=O)[C:6]2=[O:15].Cl.C([O:19][C:20](=[O:30])[CH2:21][CH:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C.CN1CCOCC1.F[P-](F)(F)(F)(F)F.[N:45]1(OC(N(C)C)=[N+](C)C)[C:49]2N=CC=C[C:48]=2[N:47]=N1>CN(C=O)C>[NH2:45][CH2:49][CH2:48][NH:47][C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]([NH:29][CH:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:21][C:20]([OH:19])=[O:30])=[O:14])[C:6]2=[O:15]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9899351HCID 9899351, compoundHCID 1557106129754-04-9

Product 1

HCID 9821989HCID 9821989, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of 8-Chloro-4-oxo-4H-quinolizine-3-carboxylic acid (22 mg, 0.098 mmol) in anhydrous DMF (1.5 ml) at room temperature was sequentially added (+/−)-3-amino-3-phenyl-propionic acid ethyl ester hydrochloride (28.4 mg, 0.123 mmol), N-methylmorpholine (32.4 μl, 0.295 mmol) and O-(7-azabenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (48.6 mg, 0.128 mmol). The resulting mixture was allowed to stir at room temperature for 2 h. The solvent was removed under vacuum and the resulting residue was subjected to a silica gel chromatography (Rex:EtOAc=1:1 to pure EtOAc) to give desired product as yellowish solid (32 mg, 81%).

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-49f247a4a3444c0faf445249dfd322c9
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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