4-Methylmorpholine → HCID 58465654, compound

HRID 1842464Notes

Reaction equation

HRID 1842464 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH2:19][CH2:18][CH2:17][N:16]2[N:20]=[C:21]([C:23](O)=[O:24])[CH:22]=[C:15]2[CH2:14]1)(=[O:12])=[O:11])([O-:3])=[O:2].[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[O:32][NH2:33].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CN1CCOCC1>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH2:19][CH2:18][CH2:17][N:16]2[N:20]=[C:21]([C:23]([NH:33][O:32][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][O:26]3)=[O:24])[CH:22]=[C:15]2[CH2:14]1)(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58465742HCID 58465742, compound

Product 1

HCID 58465654HCID 58465654, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2-nitrophenyl)sulfonyl]-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylic acid (0.116 g, 0.316 mmol) and O-(tetrahydropyran-2-yl)hydroxylamine (0.0407 g, 0.347 mmol) in methylene chloride (2.5 mL) was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.144 g, 0.379 mmol) and N-methylmorpholine (0.1 mL, 0.9 mmol). The resulting reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the residue obtained purified via silica chromatography (80-100% EtOAc/hexane) to afford Intermediate 21 as a clear colorless oil (0.152 g, 100%). LC-MS: (FA) ES+466.

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was evaporated
  3. customthe residue obtained
  4. custompurified via silica chromatography (80-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-70d0d143755d44f79e4ada64338a1deb
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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