Sodium hydride → HCID 67915666, compound

HRID 654187Notes

Reaction equation

HRID 654187 reaction equation
[NH:1]1[C:5]([SH:6])=[N:4][CH:3]=[N:2]1.[H-].[Na+].F[B-](F)(F)F.[NH2:14][C:15]1[C:57]([Cl:58])=[CH:56][C:18]([C:19]([NH:21][C@H:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][N+]3C(C4C=CC=CC=4)=CC(C4C=CC=CC=4)=CC=3C3C=CC=CC=3)[CH2:24][C@H:23]2[O:54][CH3:55])=[O:20])=[C:17]([O:59][CH3:60])[CH:16]=1>CC1C=CC=CC=1>[OH2:20].[NH2:14][C:15]1[C:57]([Cl:58])=[CH:56][C:18]([C:19]([NH:21][C@H:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][S:6][C:5]3[NH:1][N:2]=[CH:3][N:4]=3)[CH2:24][C@H:23]2[O:54][CH3:55])=[O:20])=[C:17]([O:59][CH3:60])[CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 86743794HCID 86743794, compoundHCID 178527896HCID 178527896, compound

Product 1

HCID 67915666HCID 67915666, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 2.16 parts of 1H-1,2,4-triazol-5-thiol, 1.03 parts of a sodium hydride dispersion 50% and 18 parts of methylbenzene was stirred for 3 hours at room temperature. A solution of 6.3 parts of cis-1-[2-[4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-3-methoxy-1-piperidinyl]ethyl]-2,4,6-triphenylpyridinium tetrafluoroborate in 9 parts of methylbenzene was added and stirring was continued first for 4 hours at reflux temperature and then over weekend at room temperature. The whole was extracted five times with 100 parts of a hydrochloric acid solution 1N. The combined acid aqueous phases were treated with potassium hydroxide and extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 1.24 parts (33%) of cis-4-amino-5-chloro-2-methoxy-N-[3-methoxy-1-[2-(1H-1,2,4-triazol-5-ylthio)ethyl]-4-piperidinyl]benzamide monohydrate; mp. 161.8° C. (compound 48).

Workup

  1. stirringstirring
  2. waitwas continued first for 4 hours
  3. temperatureat reflux temperature
  4. waitover weekend at room temperature
  5. extractionThe whole was extracted five times with 100 parts of a hydrochloric acid solution 1N
  6. additionThe combined acid aqueous phases were treated with potassium hydroxide
  7. extractionextracted with dichloromethane
  8. customThe extract was dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was crystallized from acetonitrile
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-f730f5e2d6ef4a10a39d72add81eda4e
Source dataset
uspto-grants-1992_07
Patent number
US05130312

Reaction notes

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