4-Methylmorpholine → HCID 46190551, compound

HRID 2359014Notes

Reaction equation

HRID 2359014 reaction equation
[CH3:1][CH:2]1[N:7]([CH3:8])[CH2:6][CH:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]([CH2:15][C:16]([O-:18])=O)[C:3]1=[O:19].[Li+].[NH2:21][C:22]1[CH:23]=[C:24]2[C:38](=[CH:39][CH:40]=1)[CH2:37][C:26]1([O:31][C:30](=[O:32])[NH:29][C:28]3[N:33]=[CH:34][CH:35]=[CH:36][C:27]1=3)[CH2:25]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[CH3:1][CH:2]1[N:7]([CH3:8])[CH2:6][CH:5]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:4]([CH2:15][C:16]([NH:21][C:22]2[CH:23]=[C:24]3[C:38](=[CH:39][CH:40]=2)[CH2:37][C:26]2([O:31][C:30](=[O:32])[NH:29][C:28]4[N:33]=[CH:34][CH:35]=[CH:36][C:27]2=4)[CH2:25]3)=[O:18])[C:3]1=[O:19]

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 58431974HCID 58431974, compound2×HCID 67392771HCID 67392771, compound

Product 1

HCID 46190551HCID 46190551, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of lithium(3,4-dimethyl-2-oxo-6-phenylpiperazin-1-yl)acetate (30 mg, 0.11 mmol) [Wood et al. US 2007/0265225], 5-amino-1,3-dihydrospiro[indene-2,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one (Intermediate 2, 27 mg, 0.10 mmol) and HATU (42 mg, 0.11 mmol) in DMF (1 mL) is treated with N-methylmorpholine (0.036 mL, 0.33 mmol). The mixture is stirred at rt for 18 h and is then purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions are combined and lyophilized to afford the title compound.

Workup

  1. customis then purified directly by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions

Sources & evidence

ORD record
ord-091a8e008bc24937b7f23c77ee65c086
Source dataset
uspto-grants-2014_04
Patent number
US08685965B2

Reaction notes

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