HCID 68576037, compound → HCID 59837523, compound

HRID 273074Notes

Reaction equation

HRID 273074 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][N:32]4[CH2:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:24][CH:23]=3)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[NH3:8].[N:11]1([C:14]([C:16]2([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][CH2:31][N:32]4[CH2:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:26][CH:27]=3)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[O:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 1

HCID 68576037HCID 68576037, compound

Product 2

HCID 222AmmoniaHCID 59837523HCID 59837523, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

4-{4-[4-(3-[1,4]Oxazepan-4-yl-propoxy)-phenyl]-tetrahydro-pyran-4-carbonyl}-piperazine-1-carboxylic acid tert-butyl ester (260 mg, 0.48 mmol) was dissolved in a solution of hydrogen chloride in dioxane (4M, 5 ml) and was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue dissolved in DCM (10 ml) and washed with saturated sodium bicarbonate solution (15 ml). The organic layer was dried over Na2SO4 and concentrated in vacuo before purifying the residue using column chromatography, eluting with a gradient of DCM:MeOH:NH3 (from 99:1:0.1 to 92:8:0.8) to afford the title compound as a white solid (80 mg, 37%). 1H NMR (400 MHz, d6-DMSO) δ 1.70-1.88 (m, 6H), 2.08 (m, 2H), 2.52-2.63 (m, 6H), 3.04-3.35 (m, 8H), 3.58 (m, 4H), 3.64 (m, 2H), 3.72 (m, 2H), 3.98 (t, 2H), 6.92 (d, 2H), 7.12 (d, 2H). LRMS ESI+ m/z 432 [MH]+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in DCM (10 ml)
  3. washwashed with saturated sodium bicarbonate solution (15 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custombefore purifying the residue
  7. washeluting with a gradient of DCM

Sources & evidence

ORD record
ord-fbe480f34c1044e5911b20596c2e8090
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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