Hydrochloric Acid → HCID 11711568, compound

HRID 853850Notes

Reaction equation

HRID 853850 reaction equation
Cl.[O:2]([CH2:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[S:15]([C:18]1[CH:26]=[CH:25][C:24]2[N:23]3[CH2:27][CH2:28][CH2:29][N:30]=[C:22]3[C:21]3(OCCC[O:31]3)[C:20]=2[CH:19]=1)(=[O:17])=[O:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH4+].[OH-]>O1CCOCC1>[O:2]([CH2:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[S:15]([C:18]1[CH:26]=[CH:25][C:24]2[N:23]3[CH2:27][CH2:28][CH2:29][N:30]=[C:22]3[C:21](=[O:31])[C:20]=2[CH:19]=1)(=[O:17])=[O:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 11648720HCID 11648720, compound

Product 1

HCID 11711568HCID 11711568, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To cold concentrated HCl (8.5 mL) was added a solution of 8′-{[(2S)-2-(phenoxymethyl)pyrrolidin-1-yl]sulfonyl}-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2-a]indole] (0.430 g, 0.889 mmol) in 1,4 dioxane (2 mL) drop-wise over a period of 20 minutes with cooling in an ice bath. The mixture was stirred at room temperature (16 hours) then heated at 53° C. (36 hours). The mixture was cooled in an ice bath, poured into ice, and basified with concentrated NH4OH to pH 11 keeping the temperature below 5° C. The organics were extracted with EtOAc (2×). The combined organic extracts were dried over MgSO4, filtered and concentrated. The crude product was flash chromatographed on Biotage KP silica gel eluting with 95/5 (EtOAc/CH3OH) to give the title compound which was dried in vacuo at 61° C. to give the analytically pure sample as an orange-brown solid (0.074 g, 19.5% yield). Anal. Calc'd for C22H23N3O4S: C, 62.10; H, 5.45; N, 9.88. Found: C, 61.89; H, 5.50; N, 9.65. NMR (400 MHz, DMSO-d6): consistent. MS: (ES+) m/z 426 [M+H]. MS: (ES−) m/z 424 [M−H]. m.p.: 159-160° C.

Workup

  1. temperaturewith cooling in an ice bath
  2. temperaturethen heated at 53° C. (36 hours)
  3. temperatureThe mixture was cooled in an ice bath
  4. additionpoured into ice
  5. customthe temperature below 5° C
  6. extractionThe organics were extracted with EtOAc (2×)
  7. dry with materialThe combined organic extracts were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed on Biotage KP silica gel eluting with 95/5 (EtOAc/CH3OH)

Sources & evidence

ORD record
ord-45a9695353004f65b09f79e56a935251
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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