4-Methylmorpholine → HCID 22313082, compound

HRID 966147Notes

Reaction equation

HRID 966147 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][O:11][CH3:12])=[O:9])=[CH:4][C:3]=1[NH:13][C:14]1[C:19]2=[C:20]([CH:26]([CH3:28])[CH3:27])[C:21]([C:23]([OH:25])=O)=[CH:22][N:18]2[N:17]=[CH:16][N:15]=1.Cl.[CH2:30]([NH2:32])[CH3:31].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C)C=O>[CH2:30]([NH:32][C:23]([C:21]1[C:20]([CH:26]([CH3:27])[CH3:28])=[C:19]2[N:18]([CH:22]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:13][C:3]1[CH:4]=[C:5]([C:8]([NH:10][O:11][CH3:12])=[O:9])[CH:6]=[CH:7][C:2]=1[F:1])=[O:25])[CH3:31]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 11198Ethylamine hydrochlorideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22313085HCID 22313085, compound

Product 1

HCID 22313082HCID 22313082, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 13 (20 mg, 0.052 mmol), ethylamine hydrochloride (6 mg, 0.08 mmol), BOP reagent (34 mg, 0.08 mmol), and N-methyl morpholine (0.012 mL, 0.1 mmol) in dimethyl formamide (0.5 mL) was stirred at RT for 18 h. The mixture was purified by reverse phase HPLC. The appropriate fractions were concentrated and the residue was converted to the HCl salt to obtain the desired product as a white solid (11 mg, 50%). LC/MS; (M+H)+=415.2

Workup

  1. customThe mixture was purified by reverse phase HPLC
  2. concentrationThe appropriate fractions were concentrated

Sources & evidence

ORD record
ord-1347be7ff319470eb44ed43a727d5117
Source dataset
uspto-grants-2005_10
Patent number
US06951859B2

Reaction notes

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