Hydrochloric Acid → HCID 21099276, compound

HRID 1351740Notes

Reaction equation

HRID 1351740 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])=[C:6]2[C:10]=1[NH:9][C:8]1[C:11]([CH2:18][CH:19]=[O:20])([CH2:15][CH2:16][CH3:17])[O:12][CH2:13][CH2:14][C:7]2=1.O.[O-:30]Cl=O.[Na+].Cl>CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[O:22])=[C:6]2[C:10]=1[NH:9][C:8]1[C:11]([CH2:18][C:19]([OH:30])=[O:20])([CH2:15][CH2:16][CH3:17])[O:12][CH2:13][CH2:14][C:7]2=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 21099275HCID 21099275, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 21099276HCID 21099276, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of [8-fluoro-5-(morpholine-4-carbonyl)-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl]-acetaldehyde (8) (99 mg, 0.255 mmol) in DMSO (3.5 mL) was added a solution of NaH2PO4 in H2O (0.36 mL of 0.7 M in H2O, 0.255 mmol) at room temperature. To the mixture was added a solution of NaClO2 in H2O (1.52 mL of 0.5 M in H2O, 0.765 mmol). After stirring for 20 hours at room temperature, the mixture was acidified with HCl. The resulting mixture was extracted with EtOAc (3×10 mL). The combined organic phase was washed with brine (20 mL), dried over Na2SO4 and concentrated. The residue was purified by preparative HPLC to give 77 mg (75%) of title compound as a white solid. Mp=98–100° C.; HRMS (ESI) [M+H]+ calculated for C21H26FN2O5 405.1820, found 405.1821; 1H NMR (DMSO-d6): 300 MHz δ 12.30 (bs, 1H), 11.45 (s, 1H), 6.95–6.85 (m, 2H), 3.92 (m, 2H), 3.66 (m, 2H), 3.45 (m, 1H), 3.15 (m, 1H), 2.94 (d, J=10.2 Hz, 2H), 2.70 (d, J=10.2 Hz, 2H), 2.59 (m, 1H), 2.57 (s, 1H), 2.51 (m, 2H), 1.99 (t, J=5.10 Hz, 2H), 1.31 (m, 1H), 0.86 (m, 1H), 0.08 (t, J=5.10 Hz, 3H). LCMS retention time: 2.073 minutes.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (3×10 mL)
  2. washThe combined organic phase was washed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0262a76a24764ad299a5983b810f03dc
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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