Thiourea → HCID 86602996, compound

HRID 1820071Notes

Reaction equation

HRID 1820071 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[NH:7][CH:6]=1)=O.[NH2:15][C:16]([NH2:18])=[S:17]>CCO>[BrH:1].[Br:14][C:11]1[CH:12]=[C:13]2[C:5]([C:3]3[N:15]=[C:16]([NH2:18])[S:17][CH:2]=3)=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 597000532-Bromo-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

Product 1

HCID 86602996HCID 86602996, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone as a light yellow solid (80 mg, 0.251 mmol) and thiourea (21 mg, 0.276 mmol) in EtOH (1 mL) was stirred at 80° C. for 1.5 h. The resulting precipitate was filtered, washed with MeOH, and dried in vacuo to give 4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamine hydrobromide salt as a beige solid (66 mg, 70% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.11 (s, 1H), 8.00 (d, J=2.5 Hz, 1H), 8.39 (t, J=2.5 Hz, 1H), 8.52 (d, J=2.0 Hz, 1H), 12.4 (s, 1H). MS: m/z 295 (M+H+).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with MeOH
  3. customdried in vacuo

Sources & evidence

ORD record
ord-55a3f51a74f047769b4d264caff45b78
Source dataset
uspto-grants-2009_10
Patent number
US07601839B2

Reaction notes

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