Acetic Acid → HCID 59837410, compound

HRID 273075Notes

Reaction equation

HRID 273075 reaction equation
[N:1]1([C:7]([C:9]2([C:15]3[CH:31]=[CH:30][C:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:17][CH:16]=3)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C=O.[C:34](O)(=O)C>C(Cl)Cl>[CH3:34][N:4]1[CH2:3][CH2:2][N:1]([C:7]([C:9]2([C:15]3[CH:16]=[CH:17][C:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:30][CH:31]=3)[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[O:8])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 59837523HCID 59837523, compound

Product 1

HCID 59837410HCID 59837410, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-{4-[4-(piperazin-1-ylcarbonyl)tetrahydro-2H-pyran-4-yl]phenoxy}propyl)-1,4-oxazepane (45 mg, 0.1 mmol) was dissolved in DCM (3 ml), to which was added formaldehyde (37% w/w in H2O, 12 mg, 0.12 mmol) and acetic acid (8 mg, 0.12 mmol) and was stirred at room temperature for 30 minutes before adding STAB (25 mg, 0.12 mmol). The solution was allowed to stir for a further 45 minutes before washing the solution with saturated sodium bicarbonate (10 ml), followed by brine (10 ml). The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the title compound as a white solid (25 mg, 56%). 1H NMR (400 MHz, d6-DMSO) δ 1.76-2.13 (m, 11H), 2.55-2.78 (m, 6H), 3.16-3.39 (m, 8H), 3.50-3.62 (m, 4H), 3.63 (m, 2H), 3.72 (M, 2H), 3.99 (t, 2H), 6.92 (d, 2H), 7.12 (d, 2H). LRMS ESI+ m/z 446 [MH]+.

Workup

  1. additionbefore adding STAB (25 mg, 0.12 mmol)
  2. stirringto stir for a further 45 minutes
  3. washbefore washing the solution with saturated sodium bicarbonate (10 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b04fa1eed31e4f008b479f363bebe1a8
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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