Hydrochloric Acid → HCID 11202787, compound

HRID 2118217Notes

Reaction equation

HRID 2118217 reaction equation
Cl[CH2:2][C:3]([O:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:22]2[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31])=[CH:24][CH:23]=2)=[C:13](\[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)/[CH2:14][CH3:15])=[CH:8][CH:7]=1)=[O:4].[Na+].[I-].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.Cl>C1COCC1.CCOC(C)=O>[N:35]1([CH2:2][C:3]([O:5][C:6]2[CH:11]=[CH:10][C:9](/[C:12](/[C:22]3[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31])=[CH:24][CH:23]=3)=[C:13](\[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)/[CH2:14][CH3:15])=[CH:8][CH:7]=2)=[O:4])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 8083MorpholineHCID 58877667HCID 58877667, compound

Product 1

HCID 11202787HCID 11202787, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred solution of compound 32 (100 mg, 0.22 mmol) in THF (4 mL) was added NaI (100 mg, 0.67 mmol) and the mixture stirred for 1 h. The reaction was cooled to 5° C. and a solution of morpholine (0.029 mL, 0.33 mmol) in THF (2 mL) was added over 1 h. After stirring for 1 h, the reaction was diluted with EtOAc (40 mL) and poured into a mixture of ice water (30 mL) and 0.1 N HCl (10 mL). The layers were separated and the organic layer was washed with brine (40 mL), dried (MgSO4) and concentrated. Et2O (8 mL) was added and the mixture was stirred for 2 h. The resulting solid was filtered, rinsed with Et2O and dried to afford the title compound, 31, as a yellow solid (68 mg, 61%). 1HNMR (400 MHz, DMSO-d6): δ 0.85 (t, 3H), 2.39 (q, 2H), 2.52 (br, 4H), 3.43 (br, 2H), 3.55 (br, 4H), 6.50 (d, J=15.9 Hz, 1H), 6.80 (d, J=8.4 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 7.09-7.19 (m, 5H), 7.24 (d, J=8.1 Hz, 2H), 7.58 (d, J=15.9 Hz, 1H), 769 (d, J=8.1 Hz, 2H), 12.33 (br s, 1H); MS m/z 498 (M+H)+.

Workup

  1. stirringAfter stirring for 1 h
  2. customThe layers were separated
  3. washthe organic layer was washed with brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. additionEt2O (8 mL) was added
  7. stirringthe mixture was stirred for 2 h
  8. filtrationThe resulting solid was filtered
  9. washrinsed with Et2O
  10. customdried

Sources & evidence

ORD record
ord-44c94100d00a412489391c9efabe6d1f
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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