Water → 3-{1-[(6-Chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-5-fluoro-1H-indol-3-yl}propan-1-amine

HRID 1835122Notes

Reaction equation

HRID 1835122 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=2)[N:9]([S:17]([C:20]2[N:27]3[C:23]([S:24][CH:25]=[CH:26]3)=[N:22][C:21]=2[Cl:28])(=[O:19])=[O:18])[CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[Cl:28][C:21]1[N:22]=[C:23]2[N:27]([C:20]=1[S:17]([N:9]1[C:10]3[C:15](=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[C:7]([CH2:6][CH2:5][CH2:4][NH2:1])=[CH:8]1)(=[O:18])=[O:19])[CH:26]=[CH:25][S:24]2

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 222197373-(3-Azidopropyl)-1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-5-fluoro-1H-indole

Product 1

HCID 222197393-{1-[(6-Chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-5-fluoro-1H-indol-3-yl}propan-1-amineYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(3-azidopropyl)-1-[(6-chloroimidazo-[2,1-b][1,3]thiazol-5-yl)sulfonyl]-5-fluoro-1H-indole (180 mg, 0.41 mmol) and triphenylphosphine (161 mg, 0.62 mmol in THF and water is stirred under nitrogen for 24 h at room temperature and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/2M NH3 in MeOH: 98/2) to afford the title product as an off-white solid, 132 mg (78% yield), mp 139-141° C., identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/2M NH3 in MeOH: 98/2)

Sources & evidence

ORD record
ord-4dd3be28f1594754921230aa46b7be5f
Source dataset
uspto-grants-2004_08
Patent number
US06770642B2

Reaction notes

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