Hydrochloric Acid → HCID 86695129, compound

HRID 1503960Notes

Reaction equation

HRID 1503960 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:21][CH2:20][C:19]2[S:18][C:17]3[C:12](=[C:13]([O:22][CH:23]4[CH2:28][CH2:27][CH:26]([N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)[CH2:25][CH2:24]4)[N:14]=[CH:15][N:16]=3)[C:11]1=2)(C(C)(C)C)(C)C.Cl>CO>[N:29]1([CH:26]2[CH2:25][CH2:24][CH:23]([O:22][C:13]3[N:14]=[CH:15][N:16]=[C:17]4[C:12]=3[C:11]3[CH:10]([CH2:9][OH:8])[CH2:21][CH2:20][C:19]=3[S:18]4)[CH2:28][CH2:27]2)[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86695127HCID 86695127, compound

Product 1

HCID 86695129HCID 86695129, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[[(tert-butyldimethylsilyl)oxy]methyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraene (350 mg, 0.69 mmol, 1.00 equiv) in methanol (30 mL) was added hydrochloric acid (3 M in water, 1 mL) was added at 0° C. and the resulting solution was stirred for 1 h at room temperature. The reaction was quenched with NaHCO3/brine and extracted with EtOAc ((3×80 mL). The organic layers were combined and dried over anhydrous sodium sulfate. After filtration and concentration in vacuo, the residue was purified by a silica gel column with DCM/MeOH (30:1-10:1) to provide 260 mg (96%) of (12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl)methanol as a light yellow semi-solid. MS (ES): m/z 390 [M+H]+.

Workup

  1. additionwas added at 0° C.
  2. customThe reaction was quenched with NaHCO3/brine
  3. extractionextracted with EtOAc ((3×80 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration in vacuo
  6. customthe residue was purified by a silica gel column with DCM/MeOH (30:1-10:1)

Sources & evidence

ORD record
ord-e4a62379617e49248819a7e1d1be1458
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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