4-Methylmorpholine → HCID 178522506, compound

HRID 536263Notes

Reaction equation

HRID 536263 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3][CH:2]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[N:41]1([S:47]([CH2:50][CH2:51][CH2:52][O:53][C:54]2[CH:55]=[CH:56][C:57]3[C:58]4[N:59]([CH2:65][CH2:66][N:67]=4)[C:60]([NH2:64])=[N:61][C:62]=3[CH:63]=2)(=[O:49])=[O:48])[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>CN(C=O)C.CCOC(C)=O>[N:41]1([S:47]([CH2:50][CH2:51][CH2:52][O:53][C:54]2[CH:55]=[CH:56][C:57]3[C:58]4[N:59]([CH2:65][CH2:66][N:67]=4)[C:60]([NH:64][C:7]([C:5]4[CH:4]=[N:3][CH:2]=[N:1][CH:6]=4)=[O:9])=[N:61][C:62]=3[CH:63]=2)(=[O:48])=[O:49])[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 78346Pyrimidine-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178508203HCID 178508203, compound

Product 1

HCID 178522506HCID 178522506, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To pyrimidine-5-carboxylic acid (95.0 mg, 0.77 mmol) in DMF (1 ml) was added HATU (342 mg, 0.9 mmol) and 4-methylmorpholine (91 mg, 0.9 mmol). The mixture was stirred for 5 min then 8-[3-(morpholin-4-ylsulfonyl)propoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Step 1, 250 mg, 0.64 mmol) in DMF (2 mL) was added. The resulting solution was allowed to stir at rt for 16 h. It was diluted with EtOAc and filtered rinsing with EtOAc and MeOH to give the title compound (195 mg, 61%). TLC Rf=0.68 in 10% MeOH/CH2Cl2, HPLC MS RT=1.13 min, MH+=500.4; 1H NMR (DMSO-d6) δ: 2.25 (2H, m), 3.21 (4H, m), 3.30 (2H, m), 3.67 (4H, m), 4.23 (2H, t), 4.31 (2H, t), 4.60 (2H, t), 7.25 (1H, d), 7.78 (1H, s), 8.16 (1H, d), 9.44 (1H, s), 9.50 (2H, s).

Workup

  1. stirringto stir at rt for 16 h
  2. filtrationfiltered
  3. washrinsing with EtOAc and MeOH

Sources & evidence

ORD record
ord-035f32fa89b9483b89b0cb389a5f49ed
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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