Hydrochloric Acid → HCID 25139337, compound

HRID 1669111Notes

Reaction equation

HRID 1669111 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:32][C:31]2[C:12](=[CH:13][C:14]3[N+:19]([O-:20])=[N:18][C:17]([CH2:21][CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[N:16][C:15]=3[CH:30]=2)[CH2:11]1)(C(C)(C)C)(C)C.Cl>CO>[N:24]1([CH2:23][CH2:22][CH2:21][C:17]2[N:18]=[N+:19]([O-:20])[C:14]3[CH:13]=[C:12]4[C:31]([CH2:32][CH:10]([CH2:9][OH:8])[CH2:11]4)=[CH:30][C:15]=3[N:16]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25139336HCID 25139336, compound

Product 1

HCID 25139337HCID 25139337, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of silyl ether 139 (488 mg, 1.07 mmol), and 1 M HCl (1.18 mL) in MeOH (30 mL) was stirred at 20° C. for 3 h. The solvent was evaporated and the residue was crystallised from MeOH/EtOAc to give alcohol 140 (357 mg, 88%) as the hydrochloride salt: mp (MeOH/EtOAc) 210-212° C.; 1H NMR [(CD3)2SO] δ 11.19 (s, 1H, HCl), 8.16 (s, 1H, H-9), 7.80 (s, 1H, H-5), 4.70 (br s, 1H, OH), 3.75-3.99 (m, 4H, 2×CH2O), 3.41 (d, J=6.6 Hz, 2H, CH2O), 3.33-3.51 (m, 2H, CH2N), 3.11-3.27 (m, 4H, CH2N, H-8), 2.87-3.11 (m, 6H, 2×CH2N, CH2), 2.59-2.71 (m, 1H, H-7), 2.22-2.32 (m, 2H, CH2); 13C NMR [(CD3)2SO] δ 163.6, 154.2, 148.4, 146.7, 131.8, 122.5, 113.8, 63.5, 63.0 (2), 55.0, 50.9 (2), 41.6, 35.4, 35.1, 33.1, 20.8. Anal. calcd for C18H24N4O3.HCl.¼CH3OH: C, 56.4; H, 6.7; N, 14.4. Found: C, 56.3; H, 6.4; N, 14.6%.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was crystallised from MeOH/EtOAc

Sources & evidence

ORD record
ord-1917fe5050ad40b9ba1f63c84ee9672a
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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