Ammonium Chloride → HCID 86711405, compound

HRID 532961Notes

Reaction equation

HRID 532961 reaction equation
C[O:2][C@@H:3]([C:5]1[N:6]=[CH:7][N:8]([C:10]2[CH:27]=[C:15]3[C:16]4[C:21]([CH2:22][CH2:23][N:14]3[C:13](=[O:28])[CH2:12][N:11]=2)=[C:20]([C:24]([CH3:26])=[CH2:25])[CH:19]=[CH:18][CH:17]=4)[CH:9]=1)[CH3:4].[CH:29]1([Mg]Br)C[CH2:30]1.[NH4+].[Cl-]>C1COCC1>[CH:24]1([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:21]=2[CH2:22][CH2:23][N:14]2[C:13](=[O:28])[CH2:12][N:11]=[C:10]([N:8]4[CH:9]=[C:5]([CH:3]([CH:4]5[CH2:30][CH2:29]5)[OH:2])[N:6]=[CH:7]4)[CH:27]=[C:15]23)[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86711397HCID 86711397, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 86711405HCID 86711405, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-(9-cyclopropyl-5-oxo-4,5,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinolin-2-yl)-1H-imidazole-4-carbaldehyde (230 mg, 0.66 mmol, it can be obtained by analogy to example 118) in THF (35 mL) was cooled to 0° C. and then treated with a solution of cPrMgBr in THF (1.39 mL, 0.70 mmol) dropwise. The mixture was stirred at 0° C. for 1 h, and an aq. solution of saturated NH4Cl was then added. The mixture was extracted with AcOEt, and the combined org. layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, AcOEt:MeOH 100:0 to 90:10) and crystallization in AcOEt gave the tile compound (66 mg). UPLC-MS: MS 389.2 (M+H+); UPLC rt 0.92 min. 1H NMR (600 MHz, DMSO-d6): δ ppm 0.21-0.46 (m, 4H); 0.58-0.70 (m, 2H); 0.91-1.00 (m, 2H); 1.08-1.25 (m, 1H); 1.91-2.04 (m, 1H); 3.01-3.17 (m, 2H); 3.88 (br s, 2H); 3.93-4.03 (m, 1H); 4.24 (br s, 2H); 4.96 (d, J=5.27 Hz, 1H); 7.12-7.25 (m, 2H); 7.25-7.35 (m, 1H); 7.49 (s, 1H); 7.91 (d, J=8.03 Hz, 1H); 8.17 (s, 1H).

Workup

  1. extractionThe mixture was extracted with AcOEt
  2. dry with materiallayers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. customby flash chromatography (SiO2, AcOEt:MeOH 100:0 to 90:10) and crystallization in AcOEt

Sources & evidence

ORD record
ord-4d0f5f6cb98647de87383b481692be0e
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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