4-Methylmorpholine → HCID 86718195, compound

HRID 1624124Notes

Reaction equation

HRID 1624124 reaction equation
CN(C(O[N:9]1N=N[C:11]2C=CC=[CH:15][C:10]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CC[O:27]CC1.[CH:30]1([CH2:36][O:37][C:38]2[C:39]3[N:40]([C:44]([C:49]([OH:51])=O)=[C:45]([CH2:47][CH3:48])[N:46]=3)[CH:41]=[CH:42][CH:43]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>CS(C)=O>[CH:30]1([CH2:36][O:37][C:38]2[C:39]3[N:40]([C:44]([C:49]([NH:9][C@H:10]([CH3:11])[CH2:15][OH:27])=[O:51])=[C:45]([CH2:47][CH3:48])[N:46]=3)[CH:41]=[CH:42][CH:43]=2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86718181HCID 86718181, compound

Product 1

HCID 86718195HCID 86718195, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.3 mg (0.044 mmol) of L-alaminol, 14 mg (0.044 mmol) of TBTU and 20 mg (0.198 mmol) of N-methylmorpholine were added to a solution of 12 mg (0.040 mmol) of 8-(cyclohexylmethoxy)-2-ethylimidazo[1,2-a]pyridine-3-carboxylic acid in 750 μl of DMSO, and the mixture was then shaken at room temperature overnight. The mixture was then purified by preparative HPLC (Method 6), giving 12 mg (84% of theory) of 8-(cyclohexylmethoxy)-2-ethyl-N-[(2R)-1-hydroxypropan-2-yl]imidazo[1,2-a]pyridine-3-carboxamide as formic acid salt.

Workup

  1. customThe mixture was then purified by preparative HPLC (Method 6)

Sources & evidence

ORD record
ord-c40c982cbe0f42b78da7ed515cf6ca58
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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