Dimethylformamide → HCID 178511071, compound

HRID 2237628Notes

Reaction equation

HRID 2237628 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:29])[N:9]([C:13]3[CH:18]=[CH:17][C:16]([C@H:19]4[CH2:24][CH2:23][C@H:22]([CH2:25][C:26]([NH2:28])=O)[CH2:21][CH2:20]4)=[CH:15][CH:14]=3)[CH2:10][CH2:11][O:12][C:6]=2[N:5]=[CH:4][N:3]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O>C1COCC1>[NH2:1][C:2]1[C:7]2[C:8](=[O:29])[N:9]([C:13]3[CH:14]=[CH:15][C:16]([C@H:19]4[CH2:20][CH2:21][C@H:22]([CH2:25][C:26]#[N:28])[CH2:23][CH2:24]4)=[CH:17][CH:18]=3)[CH2:10][CH2:11][O:12][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178513913HCID 178513913, compound

Product 1

HCID 178511071HCID 178511071, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred slurry of 2-{trans-4-[4-(4-amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)phenyl]cyclohexyl}acetamide (45 mg, 0.11 mmol), from Example 30, in THF (1 mL) was added DMF (0.002 mL) and oxalyl chloride (0.05 mL, 0.6 mmol). After two hours of stirring at room temperature, the reaction was quenched with aqueous sodium bicarbonate and extracted with EtOAc. The organic layer was washed with water, dried over sodium sulfate and concentrated in vacuo to afford the title compound as a light-yellow colored solid, 34 mg. 1H NMR (400 MHz, DMSO-d6): δ 8.17 (s, 1H), 7.63 (br s, 2H) 7.22 (m, 4H), 4.57 (m, 2H), 3.90 (m, 2H), 2.43 (m, 3H), 1.78 (m, 4H), 1.63 (m, 1H), 1.43 (m, 2H), 1.08 (m, 2H). m/z=378.3 (M+1). IC50 64.3 nM (range 51.2-91.1 nM).

Workup

  1. customthe reaction was quenched with aqueous sodium bicarbonate
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71f421057a93497bac5947527665fa69
Source dataset
uspto-grants-2010_05
Patent number
US07718645B2

Reaction notes

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