Water → HCID 51352791, compound

HRID 1408532Notes

Reaction equation

HRID 1408532 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([CH:17]3[CH2:19][CH2:18]3)=[CH:15][C:14]([CH:20]3[CH2:22][CH2:21]3)=[N:13]2)=[CH:8][CH:7]=1)=[O:4].[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.[H-].[Na+].O>CN(C=O)C.CCOC(C)=O>[CH:20]1([C:14]2[CH:15]=[C:16]([CH:17]3[CH2:19][CH2:18]3)[N:12]([C:9]3[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:7][CH:8]=3)[N:13]=2)[CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 24758Sodium hydrideHCID 67197968HCID 67197968, compound

Product 1

HCID 51352791HCID 51352791, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Intermediate 41 (150 mg, 0.475 mmol) and morpholine (40 mg, 0.475 mmol) were dissolved in DMF (3 mL) at 0° C. and Sodium Hydride (30 mg, 1.25 mmol) was added to the reaction mixture. Reaction was allowed to stir at ambient temperature overnight. Work-up (H2O:AcOEt) followed by purification on column afforded the title compound as a white solid. M.P. 178-184° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 9.87 (s, 1H), 7.74 (d, J 8.7, 2H), 7.49 (d, J 8.7, 2H), 5.77 (s, 1H), 3.63 (t, J 4.2, 4H), 3.13 (s, 2H), 2.48-2.45 (m, 4H), 1.89-1.69 (m, 2H), 0.92-0.81 (m, 4H), 0.69-0.60 (m, 4H). MS (m/z): 367.32 [M+H]+.

Workup

  1. customReaction
  2. customfollowed by purification on column

Sources & evidence

ORD record
ord-b8434b624e634b58a2a68ab14b0a676c
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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