4-Methylmorpholine → HCID 57988757, compound

HRID 889020Notes

Reaction equation

HRID 889020 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][C:20]#[C:21][C:22]4[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=4)[C:25](O)=[O:26])[CH:18]=3)[N:6]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:5]=2[C:4](=[O:39])[N:3]1[CH2:40][CH2:41][CH3:42].C(=O)([O-])[O-].[NH4+].[NH4+].C1C=CC2N(O)N=[N:55]C=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][C:20]#[C:21][C:22]4[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=4)[C:25]([NH2:55])=[O:26])[CH:18]=3)[N:6]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:38])[CH3:37])[C:5]=2[C:4](=[O:39])[N:3]1[CH2:40][CH2:41][CH3:42]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 517111Ammonium CarbonateHCID 57988758HCID 57988758, compound

Product 1

HCID 57988757HCID 57988757, compoundYield 32.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(3-{4-[2,6-dioxo-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]-pyrazol-1-yl}-prop-1-ynyl)-benzoic acid (100 mg, 0.17 mmol), ammonium carbonate (33 mg, 0.34 mmol), HOBT (36 mg, 0.24 mmol), N-methyl morpholine (34 mg, 0.34 mmol) were taken in DMF (2 ml), EDCI (130 mg, 0.68 mmol) was added at cold condition and stirred for 18 hrs at room temperature. The reaction mixture was diluted with water (10 ml) and extracted with DCM (3×5 ml), the organic layer was washed with brine (2×10 ml), dried over Na2SO4. The organic solvent was evaporated and the crude product was purified using HPLC to obtain 3-(3-{4-[2,6-Dioxo-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]-pyrazol-1-yl}-prop-1-ynyl)-benzamide (33 mg, 18%).

Workup

  1. extractionextracted with DCM (3×5 ml)
  2. washthe organic layer was washed with brine (2×10 ml)
  3. dry with materialdried over Na2SO4
  4. customThe organic solvent was evaporated
  5. customthe crude product was purified

Sources & evidence

ORD record
ord-85c033ddb4c24f2bb062955cfd900936
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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