Nitrogen → HCID 67958869, compound

HRID 527245Notes

Reaction equation

HRID 527245 reaction equation
N#N.[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[C:7]([C:9]([OH:11])=O)[N:8]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.[C:50]([O:56][C:57]1([C:60]2[N:61]=[C:62]([CH2:65][N:66]3[N:70]=[C:69]([NH2:71])[CH:68]=[N:67]3)[O:63][CH:64]=2)[CH2:59][CH2:58]1)(=[O:55])[C:51]([CH3:54])([CH3:53])[CH3:52]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:50]([O:56][C:57]1([C:60]2[N:61]=[C:62]([CH2:65][N:66]3[N:70]=[C:69]([NH:71][C:9]([C:7]4[N:8]=[C:4]([CH3:3])[O:5][C:6]=4[C:12]4[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=4)=[O:11])[CH:68]=[N:67]3)[O:63][CH:64]=2)[CH2:59][CH2:58]1)(=[O:55])[C:51]([CH3:54])([CH3:53])[CH3:52]

Participants

9

Reactant 6

HCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 669292052-Methyl-5-(m-tolyl)oxazole-4-carboxylic acidHCID 67958713HCID 67958713, compound

Product 1

HCID 67958869HCID 67958869, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 2-methyl-5-(m-tolyl)oxazole-4-carboxylic acid (WO 2009/077990) (92 mg, 0.42 mmol) in CH2Cl2 (2.0 mL) was treated successively with DMAP (13 mg, 0.11 mmol), HOBt (69 mg, 0.51 mmol), EDC.HCl (203 mg, 1.06 mmol) and DIPEA (0.29 mL, 1.69 mmol) and the mixture was stirred at rt for 30 min. A solution of 1-(2-((4-amino-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)cyclopropyl pivalate (129 mg, 0.42 mmol) in CH2Cl2 (2.0 mL) was then added and the reaction mixture was stirred at rt overnight. The reaction mixture was then diluted with CH2Cl2 (10 mL), the layers were separated and the org. layer was washed with water (10 mL), dried over MgSO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a white foam: TLC: rf (2:1 hept-EA)=0.25. LC-MS-conditions 06: tR=1.10 min, [M+H]+=505.37.

Workup

  1. stirringthe reaction mixture was stirred at rt overnight
  2. customthe layers were separated
  3. washlayer was washed with water (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customPurification of the residue by FC (2:1 hept-EA)

Sources & evidence

ORD record
ord-6513f77aa39d4d83a0aa20b77a2d1db4
Source dataset
uspto-grants-2016_05
Patent number
US09346793B2

Reaction notes

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