Triethylamine → HCID 59367661, compound

HRID 2079795Notes

Reaction equation

HRID 2079795 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH2:7]([O:11][CH:12]([O:14][NH:15][C:16]([C:18]1[CH:19]=[N:20][C:21]([N:24]2[CH2:29][CH:28]3[CH:26]([CH:27]3[NH:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=3)[CH2:25]2)=[N:22][CH:23]=1)=[O:17])[CH3:13])[CH:8]([CH3:10])[CH3:9].[CH2:42]([N:44]([CH2:47]C)[CH2:45][CH3:46])[CH3:43]>CN(C=O)C.C(Cl)Cl>[CH2:7]([O:11][CH:12]([O:14][NH:15][C:16]([C:18]1[CH:19]=[N:20][C:21]([N:24]2[CH2:25][CH:26]3[CH:28]([CH:27]3[N:30]([C:1](=[O:5])[CH2:2][CH2:47][N:44]([CH2:45][CH3:46])[CH2:42][CH3:43])[CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=3)[CH2:29]2)=[N:22][CH:23]=1)=[O:17])[CH3:13])[CH:8]([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59367561HCID 59367561, compound

Product 1

HCID 59367661HCID 59367661, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-N,N-Diethylaminopropionic acid (73 mg, 0.5 mmol) was suspended in oxalyl chloride (1 ml, 11.2 mmol) and DMF (1 drop) was added. The resultant mixture was stirred at r.t. overnight. The reaction mixture was then evaporated under reduced pressure and azeotroped with DCM. The residue was dissolved in DCM (1 ml) and added to an ice-cooled solution of N-(1-isobutoxyethoxy) 2-{6-[(naphthalen-2-ylmethyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}-pyrimidine-5-carboxamide (100 mg, 0.21 mmol) in DCM (3 ml) and triethylamine (0.3 ml, 2.15 mmol). After stirring at 0° C. for 20 min, the resulting mixture was stirred at r.t. overnight. The reaction mixture was partitioned between DCM (5 ml) and water (5 ml). The aqueous layer was extracted twice more with DCM (2×5 ml) and the combined organics washed with brine (2×5 ml), dried (MgSO4) and evaporated to dryness. The title compound was obtained as a white solid (199 mg, quant.). m/z 603 [M+H]+.

Workup

  1. customThe reaction mixture was then evaporated under reduced pressure
  2. customazeotroped with DCM
  3. dissolutionThe residue was dissolved in DCM (1 ml)
  4. additionadded to an ice-
  5. stirringthe resulting mixture was stirred at r.t. overnight
  6. customThe reaction mixture was partitioned between DCM (5 ml) and water (5 ml)
  7. extractionThe aqueous layer was extracted twice more with DCM (2×5 ml)
  8. washthe combined organics washed with brine (2×5 ml)
  9. dry with materialdried (MgSO4)
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-5d0ae6c5ea6a427088b905bd025adc21
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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