Hydrochloric Acid → HCID 178483168, compound

HRID 1194316Notes

Reaction equation

HRID 1194316 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[O:11][C:12]([C:15](=O)[N:16]([CH3:18])[CH3:17])=[CH:13][CH:14]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3].B#B.Cl>O1CCCC1.O>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]2[O:11][C:12]([CH2:15][N:16]([CH3:18])[CH3:17])=[CH:13][CH:14]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 178484432HCID 178484432, compound

Product 1

HCID 178483168HCID 178483168, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 676 mg. (2.43 mmole) of 2-guanidino-4-(5-[N,N-dimethylcarbamoyl]-2-furyl)thiazole in 25 ml. of tetrahydrofuran was added dropwise, at room temperature, 24.9 ml. (24.3 mmole) of a 0.97M solution of diborane in tetrahydrofuran. Stirring was continued for 5 hours at room temperature and then 15 ml. of 6N hydrochloric acid was added slowly, keeping the temperature below 30° C. Stirring was continued for 30 minutes, and then the mixture was diluted with water and washed with ethyl acetate. The resulting aqueous phase was made alkaline with 1N sodium hydroxide solution and the solid which precipitated was recovered by filtration, to give 340 mg. of the title compound, mp greater than 200° C.

Workup

  1. customthe temperature below 30° C
  2. stirringStirring
  3. waitwas continued for 30 minutes
  4. washwashed with ethyl acetate
  5. customthe solid which precipitated
  6. filtrationwas recovered by filtration
  7. customto give 340 mg

Sources & evidence

ORD record
ord-8a63622efafe43c0a0b46a3826cb8040
Source dataset
uspto-grants-1989_03
Patent number
US04814341

Reaction notes

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