Water → HCID 19044694, compound

HRID 1682507Notes

Reaction equation

HRID 1682507 reaction equation
O.[CH3:2][S:3]([OH:6])(=[O:5])=[O:4].[F:7][C:8]1[C:16]2[N:15]([CH3:17])[C:14]3[CH2:18][CH2:19][N:20]([CH2:23][C:24]4[N:25]=[CH:26][NH:27][C:28]=4[CH3:29])[C:21](=[O:22])[C:13]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1>C(O)CC>[OH2:4].[OH2:22].[CH3:2][S:3]([OH:6])(=[O:5])=[O:4].[F:7][C:8]1[C:16]2[N:15]([CH3:17])[C:14]3[CH2:18][CH2:19][N:20]([CH2:23][C:24]4[N:25]=[CH:26][NH:27][C:28]=4[CH3:29])[C:21](=[O:22])[C:13]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 172999Lurosetron

Product 1

HCID 19044694HCID 19044694, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
65 °C

Procedure

Water (0.29 l) and methanesulphonic acid (0.23 l) was added to a suspension of 6-fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indol-1-one (1.04 kg) in propan-1-ol (7.4 l). The mixture was heated to about 65° C. to give a clear solution, which was filtered, and the filter rinsed with propan-1-ol. The combined filtrate and wash were cooled to about 15° C. and diisopropyl ether (7.9 l) was added to the resulting suspension. The mixture was cooled to 5° C., and the solid isolated by filtration, washed with diisopropyl ether:propan-1-ol (3:1, 2×1.8 l) and diisopropyl ether (2×2 l) and finally dried in vacuo at about 35° C. to yield the title compound (1.39 kg).

Workup

  1. customto give a clear solution, which
  2. filtrationwas filtered
  3. washthe filter rinsed with propan-1-ol
  4. washThe combined filtrate and wash
  5. temperaturewere cooled to about 15° C.
  6. additiondiisopropyl ether (7.9 l) was added to the resulting suspension
  7. temperatureThe mixture was cooled to 5° C.
  8. customthe solid isolated by filtration
  9. washwashed with diisopropyl ether:propan-1-ol (3:1, 2×1.8 l) and diisopropyl ether (2×2 l)
  10. customfinally dried in vacuo at about 35° C.

Sources & evidence

ORD record
ord-72bb633e86004fb6a91d31fe919028c7
Source dataset
uspto-grants-1997_06
Patent number
US05635513

Reaction notes

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