4-Methylmorpholine → HCID 68323469, compound

HRID 1748354Notes

Reaction equation

HRID 1748354 reaction equation
[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([OH:18])=O)=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CN1CCOCC1.[CH3:50][C:51]1([CH3:65])[C:55]([CH3:57])([CH3:56])[O:54][B:53]([C:58]2[CH:59]=[C:60]([CH:62]=[CH:63][CH:64]=2)[NH2:61])[O:52]1>CN(C=O)C.O>[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([NH:61][C:60]4[CH:62]=[CH:63][CH:64]=[C:58]([B:53]5[O:54][C:55]([CH3:57])([CH3:56])[C:51]([CH3:65])([CH3:50])[O:52]5)[CH:59]=4)=[O:18])=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27346553-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672357061-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid2×

Product 1

HCID 68323469HCID 68323469, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 2.3 g, 9.2 mmol) in DMF (30 mL) are added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (3.7 g, 9.7 mmol) and N-methylmorpholine (2.5 mL, 22.5 mmol). The reaction mixture is stirred for 1 h at room temperature and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.4 g, 11.1 mmol) is added. The reaction mixture is stirred for 16 h at room temperature and is poured into water (200 mL). The resulting solid is collected by filtration, rinsed with water and dried to afford the title compound (3.8 g, 92%).

Workup

  1. stirringThe reaction mixture is stirred for 16 h at room temperature
  2. filtrationThe resulting solid is collected by filtration
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-3eedbfca3fa4450c8bbdaa1e6924b930
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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