Morpholine → HCID 71512863, compound

HRID 2406309Notes

Reaction equation

HRID 2406309 reaction equation
[Cl:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>CN(C=O)C.C(Cl)Cl.O>[Cl:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]([CH3:11])=[C:6]([C:7]([N:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)=[O:9])[CH:10]=1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 715128585-Chloro-2-methyl-4-nitrobenzoic acid

Product 1

HCID 71512863HCID 71512863, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 5-chloro-2-methyl-4-nitrobenzoic acid (197 mg, 0.91 mmol) in DMF (5 mL) was added triethylamine (0.13 mL, 0.91 mmol) and HATU (345 mg, 0.91 mmol) followed by morpholine (0.08 mL, 0.91 mmol). The mixture was allowed to stir at RT for 18 h and then water (10 mL) and DCM were added. The organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane) gave (5-chloro-2-methyl-4-nitrophenyl)(morpholino)methanone (244 mg, 95%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M+H]+=285 at 3.05 min. 1H NMR (400 MHz, CDCl3): δ 7.76 (s, 1H), 7.36 (s, 1H), 3.83-3.76 (m, 4H), 3.66-3.58 (m, 2H), 3.28-3.20 (m, 2H), 2.37 (s, 3H).

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-a52b4d4b47124ebbb7ff4128dea7abf3
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

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