4-Methylmorpholine → HCID 86638103, compound

HRID 907384Notes

Reaction equation

HRID 907384 reaction equation
[CH2:1]([C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:22])[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=2)=[O:13])=[N:8][C:7]=1[C:23]([OH:25])=O)[CH2:2][CH:3]([CH3:5])[CH3:4].CN1CCOCC1.[N:33]1([CH2:39][CH2:40][NH2:41])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:22])[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=2)=[O:13])=[N:8][C:7]=1[C:23]([NH:41][CH2:40][CH2:39][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)=[O:25])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 4082852-MorpholinoethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86638099HCID 86638099, compound

Product 1

HCID 86638103HCID 86638103, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Isopentyl-2-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-1,3-thiazole-4-carboxylic acid (330 mg, 0.90 mmol; see Preparation 3(iv) above) was dissolved in DMF (2.5 mL, dry), to which was added NMM (0.1 mL, dry), 2-(4-morpholinyl)ethanamine (117 mg, 0.90 mmol), and HBTU (682 mg, 1.80 mmol) at room temperature with stirring. The stirring was continued at room temperature for 24 h and then the reaction mixture was extracted with sodium hydroxide solution (381 mg, 9.52 mmol in water 10 mL) and ethyl acetate (3×50 mL). The organic layers were collected, dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by column chromatography using ethyl acetate/methanol containing 1% TEA as eluent (RF=0.15). The sub-title compound was obtained as pale yellow solid (400 mg, 93%).

Workup

  1. customThe organic layers were collected
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-4720bfb03e404b849df705a36138540c
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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