Dimethylformamide → HCID 67966880, compound

HRID 527553Notes

Reaction equation

HRID 527553 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([CH2:13][CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])[CH3:3].CN(C)C=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:42][C:43]1([CH3:60])[C:47]2[C:48]([O:52][C:53]3[N:58]=[CH:57][C:56]([NH2:59])=[CH:55][N:54]=3)=[CH:49][CH:50]=[CH:51][C:46]=2[O:45][CH2:44]1>C(OCC)(=O)C>[CH3:42][C:43]1([CH3:60])[C:47]2[C:48]([O:52][C:53]3[N:54]=[CH:55][C:56]([NH:59][C:10]([C@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:13][CH3:14])=[O:12])=[CH:57][N:58]=3)=[CH:49][CH:50]=[CH:51][C:46]=2[O:45][CH2:44]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2755936(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acidHCID 679585232-[(3,3-Dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-pyrimidinamine2×

Product 1

HCID 67966880HCID 67966880, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoic acid (20.14 mg, 0.099 mmol) in N,N-dimethylformamide (1.5 mL) DIPEA (0.029 mL, 0.165 mmol) and TBTU (33.9 mg, 0.106 mmol) were added. The mixture reaction was stirred during 15 minutes at room temperature, then 2-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-pyrimidinamine (Intermediate 65, 17 mg) was added. The reaction mixture was stirred during 48 hours at room temperature. The mixture was diluted with ethyl acetate (5 ml) and washed with brine (3×5 ml). The organic layer was separated, dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel flash chromatography using a 10 g-SNAP column and cyclohexane/ethyl acetate from 100/0 to 40/60 as eluent to afford the title compound as a white solid (4.4 mg).

Workup

  1. customThe mixture reaction
  2. stirringThe reaction mixture was stirred during 48 hours at room temperature
  3. washwashed with brine (3×5 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-531ef8dcb86b45d69e5b0e3927f2e94a
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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