1,3,4-Thiadiazol-2-amine → HCID 9821215, compound

HRID 1611405Notes

Reaction equation

HRID 1611405 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16](=[O:20])[C:17](Cl)=[O:18])=[CH:8]2)=[CH:4][CH:3]=1.[NH2:23][C:24]1[S:25][CH:26]=[N:27][N:28]=1>COCCOC>[S:25]1[CH:26]=[N:27][N:28]=[C:24]1[NH:23][C:17](=[O:18])[C:16]([C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:6][C:5]2[CH:21]=[CH:22][C:2]([F:1])=[CH:3][CH:4]=2)[CH:8]=1)=[O:20]

Participants

4

Reactant 2

HCID 199091,3,4-Thiadiazol-2-amineHCID 11056170HCID 11056170, compound

Product 1

HCID 9821215HCID 9821215, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-(1-(4-fluorobenzyl)-1H-indol-3-yl)-2-oxo-acetyl chloride (318 mg) in dry 1,2-dimethoxyethane (5 ml) is added dropwise to a suspension of 2-amino-1,3,4-thiadiazole (91 mg) and dry, ground K2CO3 (138 mg) in 5 ml of 1,2-dimethoxyethane, operating at room temperature. The reaction mixture is left under stirring for 12 hours then poured into water (60 ml). The resulting suspension is stirred for 30 minutes. The precipitate is filtered off and suspended in methanol (10 ml) under stirring for 30 minutes. The solid is recovered by filtration and dried to give N-(1,3,4-thiadiazol-2-yl)-2-(1-(4-fluorobenzyl)-1H-indol-3-yl)-2-oxo-acetamide (168 mg).

Workup

  1. customdry
  2. customoperating at room temperature
  3. waitThe reaction mixture is left
  4. additionthen poured into water (60 ml)
  5. stirringThe resulting suspension is stirred for 30 minutes
  6. filtrationThe precipitate is filtered off
  7. stirringunder stirring for 30 minutes
  8. filtrationThe solid is recovered by filtration
  9. customdried

Sources & evidence

ORD record
ord-aaa30b08c04d4499a183d4d94c203327
Source dataset
uspto-grants-2006_01
Patent number
US06987122B2

Reaction notes

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