Cyclopropylthiourea → cyclopropyl-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-amine

HRID 2108732

Reaction equation

HRID 2108732 reaction equation
Br[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=O.[CH:14]1([NH:17][C:18]([NH2:20])=[S:19])[CH2:16][CH2:15]1>C(O)C>[CH:14]1([NH:17][C:18]2[S:19][CH:2]=[C:3]([C:5]3[C:13]4[C:8](=[N:9][CH:10]=[CH:11][CH:12]=4)[NH:7][CH:6]=3)[N:20]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 2560481CyclopropylthioureaHCID 132853562-bromo-1-(1H-pyrrolo(2,3-b)pyridin-3-yl)ethan-1-one

Product 1

HCID 11615827cyclopropyl-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-amineYield 124.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-Bromo-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone (prepared according to Galvez C. et al, J. Het. Chem. 21, 1984, p421-423) (0.90 g, 3.76 mmol) and cyclopropyl-thiourea (prepared according to Marletta, M. et al, J. Med. Chem. 35, 1992, p1137-1144) (0.46 g, 3.96 mmol) was heated in ethanol (20 mL), at reflux for 4 hours. The reaction mixture was cooled to 0° C. with and ice-water bath, then the solids were filtered and dried to give cyclopropyl-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-amine as a tan solid (1.2 g, 92%). LC/MS MH+ =257.02, LC/MS RT: 1.62 min. 1H NMR (500 MHz, DMSO-d6, ppm) 12.22 (s,1H), 9.20 (bs,1H), 8.42 (d,1H, J=7.82 Hz), 8.36 (dd,1H, J=4.81, 1.22 Hz), 8.00 (s,1H), 7.25 (m,1H), 6.12 (s,1H), 2.77 (t, 1H,J=4.75), 0.86 (m,2H), 0.71 (m,2H).

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationthe solids were filtered
  3. customdried

Sources & evidence

ORD record
ord-e761e45158a141959269b7d77abd68d7
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Linked notes

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