Dimethylformamide → HCID 59367659, compound

HRID 2079798Notes

Reaction equation

HRID 2079798 reaction equation
[N:1]1([CH:7]2[CH:12]3[CH:8]2[CH2:9][N:10]([C:13]2[N:18]=[CH:17][C:16]([C:19](O)=[O:20])=[CH:15][N:14]=2)[CH2:11]3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CCN=C=N[CH2:27][CH2:28][CH2:29]N(C)C.Cl.C1C=CC2[N:42]([OH:43])N=NC=2C=1.C(N([CH2:49][CH3:50])CC)C.CN([CH:54]=[O:55])C>O>[CH2:54]([O:55][CH:49]([O:43][NH:42][C:19]([C:16]1[CH:15]=[N:14][C:13]([N:10]2[CH2:11][CH:12]3[CH:8]([CH:7]3[N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[CH2:9]2)=[N:18][CH:17]=1)=[O:20])[CH3:50])[CH:28]([CH3:27])[CH3:29]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59367641HCID 59367641, compound

Product 1

HCID 59367659HCID 59367659, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude 2-(6-Morpholin-4-yl-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylic acid was suspended in anhydrous DMF (3 ml) and EDCl (19 mg, 0.1 mmol) and HOBt (11 mg, 0.075 mmol) were added. After stirring for ˜5 minutes, triethylamine (35 μl, 0.25 mmol) and intermediate D (58 μl, 0.5 mmol) were added and the resultant mixture was stirred at r.t. for 18 h. The reaction mixture was diluted with water and extracted with EtOAc (3×10 ml) and DCM (2×10 ml). The combined organics were dried (MgSO4) and evaporated onto silica. The residue was purified by flash chromatography eluting with 100% DCM to 15% MeOH/DCM to give the title compound as an off-white solid (10 mg, 51%). LCMS purity 100%, m/z 406 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×10 ml) and DCM (2×10 ml)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated onto silica
  4. customThe residue was purified by flash chromatography
  5. washeluting with 100% DCM to 15% MeOH/DCM

Sources & evidence

ORD record
ord-801a97e2e2f14c02b3f8cd41c0a6299e
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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