Morpholine → HCID 68060960, compound

HRID 1520054Notes

Reaction equation

HRID 1520054 reaction equation
CCOC(C(C#N)=N[O:8][C:9]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([C:37]2[N:38]=[N:39][N:40]([C:42]3[CH:47]=[CH:46][C:45]([CH2:48]C(O)=O)=[CH:44][CH:43]=3)[CH:41]=2)=[N:29]1.CCN(C(C)C)C(C)C.N1CCOCC1>CN(C=O)C.CCOC(C)=O>[N:13]1([C:9](=[O:8])[CH2:48][C:45]2[CH:46]=[CH:47][C:42]([N:40]3[CH:41]=[C:37]([C:30]4[C:31]5[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=5)[NH:28][N:29]=4)[N:38]=[N:39]3)=[CH:43][CH:44]=2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 67981065HCID 67981065, compoundHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate

Product 1

HCID 68060960HCID 68060960, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

COMU (151 mg; 0.41 mmol; 1.3 eq.) was added into a solution of {4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]phenyl}acetic acid (100 mg; 0.31 mmol; 1.0 eq.) and DIEA (69 μl; 0.41 mmol; 1.3 eq.) in DMF (4 mL). After 1-2 min, morpholine (33 μl; 0.38 mmol; 1.2 eq.) was added and the reaction mixture was stirred overnight at RT. EtOAc was added and the reaction mixture was washed twice with an aqueous saturated solution of NaHCO3. The organic layer was dried over magnesium sulfate, filtered and concentrated. Purification by preparative HPLC afforded the tittle compound as a white solid. 1H NMR (300 Mz, DMSO-d6) δ: 13.36 (brs, 1H), 9.29 (s, 1H), 8.36 (d, J=8.1 Hz, 1H), 7.99 (d, J=8.5 Hz, 2H), 7.61 (d, J=8.5 Hz, 1H), 7.49-7.41 (m, 3H), 7.28-7.23 (m, 1H), 3.84 (s, 2H), 3.58-3.55 (m, 6H), 3.49-3.46 (m, 2H). HPLC (Condition A): Rt 2.97 min (purity 98.8%). MS (ESI+): 389.3, MS (ESI−): 387.3.

Workup

  1. washthe reaction mixture was washed twice with an aqueous saturated solution of NaHCO3
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-e75d4440b1984f4bb09534ecff2cc63e
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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