Hydrochloric Acid → HCID 25073814, compound

HRID 1027893Notes

Reaction equation

HRID 1027893 reaction equation
[CH2:1]1[CH:9]2[CH:4]([CH2:5][NH:6][CH2:7][CH2:8]2)[CH2:3][N:2]1[C:10]1[C:11]2[CH2:21][CH2:20][CH2:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:12]=2[N:13]=[C:14]([NH2:16])[N:15]=1.C=O.[BH3-][C:29]#N.[Na+].Cl>CC#N>[CH3:29][N:6]1[CH2:7][CH2:8][CH:9]2[CH2:1][N:2]([C:10]3[C:11]4[CH2:21][CH2:20][CH2:19][C:18]5[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=5[C:12]=4[N:13]=[C:14]([NH2:16])[N:15]=3)[CH2:3][CH:4]2[CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 25074116HCID 25074116, compound

Product 1

HCID 25073814HCID 25073814, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

The product from Example 79B (20.4 mg, 0.061 mmol) was treated with 0.091 M formaldehyde in CH3CN (0.80 mL, 0.073 mmol), diluted with CH3CN (2.24 mL), treated with NaCNBH3 (7.6 mg, 0.12 mmol), treated dropwise with a solution of 0.48 M HCl in CH3CN to keep the reaction at approximately a pH of 6 and then stirred for 1 hour. The mixture was directly purified by chromatography on silica gel (2, 3.5 and 5% (9:1 MeOH:saturated aqueous NH4OH) in CH2Cl2) to provide 9.6 mg of the title compound. The 0.48 M HCl in CH3CN was prepared by diluting 1 mL of concentrated HCl to 25 mL with CH3CN. The 0.091 M formaldehyde solution was prepared by diluting 37% aqueous formaldehyde with CH3CN. 1H NMR (CDCl3) δ 1.63-1.76 (m, 1H), 1.76-1.89 (m, 1H), 2.10-2.21 (m, 2H), 2.21-2.36 (m, 3H), 2.28 (s, 3H), 2.37-2.55 (m, 5H), 2.65 (t, J=6.78 Hz, 2H), 3.55 (dd, J=10.85, 5.43 Hz, 1H), 3.62-3.75 (m, 3H), 4.77 (s, 2H), 7.18-7.23 (m, 1H), 7.29-7.39 (m, 2H), 7.75-7.79 (m, 1H); MS (M+H)+ m/z 350.

Workup

  1. customthe reaction at approximately a pH of 6
  2. customThe mixture was directly purified by chromatography on silica gel (2, 3.5 and 5% (9:1 MeOH:saturated aqueous NH4OH) in CH2Cl2)

Sources & evidence

ORD record
ord-07bc33603bdd46028647db6560fdf121
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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