Hydrochloric Acid → HCID 86661313, compound

HRID 1685079Notes

Reaction equation

HRID 1685079 reaction equation
CP(C)C.[N:5]([CH2:8][C:9]1[N:10]=[C:11]([NH:14][C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[O:16])[S:12][CH:13]=1)=[N+]=[N-].[ClH:26]>C1COCC1>[ClH:26].[NH2:5][CH2:8][C:9]1[N:10]=[C:11]([NH:14][C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[O:16])[S:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68983TrimethylphosphineHCID 86661312HCID 86661312, compound

Product 1

HCID 86661313HCID 86661313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trimethylphosphine (107 μL, 1.2 mmol) was added dropwise to a THF (5 mL) solution of 1-(4-(azidomethyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea (307 mg, 1.0 mmol) at 0 C under a nitrogen atmosphere. The mixture was stirred for 22 hours then HCl (0.5 mL, 4M in water) was added and the stirring was continued for 22 hours. Upon evaporation of the mixture, the product was recrystallized from acetonitrile to afford 1-(4-(aminomethyl) thiazol-2-yl)-3-(3-fluorobenzyl)urea hydrochloride. 1H NMR (400 MHz, CD3OD): δ 10.3 (1H, br), 7.34 (m, 1H), 7.17-6.95 (m, 4H), 4.45 (s, 2H), 4.08 (s, 2H). MS (ES+): M/Z 281 (M+H)+.

Workup

  1. waitthe stirring was continued for 22 hours
  2. customUpon evaporation of the mixture
  3. customthe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-792c87b0ea1d4ef0b097960fcb9390d3
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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