Thiourea → 4-(9H-pyrido[2,3-b]indol-6-yl)thiazol-2-amine

HRID 341282Notes

Reaction equation

HRID 341282 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]1[N:14]=[CH:15][CH:16]=[CH:17][C:8]2=1)=O.[NH2:18][C:19]([NH2:21])=[S:20]>CCO>[N:14]1[C:9]2[NH:10][C:11]3[C:7]([C:8]=2[CH:17]=[CH:16][CH:15]=1)=[CH:6][C:5]([C:3]1[N:18]=[C:19]([NH2:21])[S:20][CH:2]=1)=[CH:13][CH:12]=3

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 585145292-bromo-1-(9H-pyrido[2,3-b]indol-6-yl)ethanone

Product 1

HCID 585144664-(9H-pyrido[2,3-b]indol-6-yl)thiazol-2-amineYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred suspension of 2-Bromo-1-(9H-pyrido[2,3-b]indol-6-yl)ethanone (100 mg, 0.346 mmol) in EtOH (2 mL) was added thiourea (26 mg, 1 equiv.) and the mixture was heated at 70° C. for 2 h. After cooling to room temperature, the solvent was evaporated to dryness. The resulting solid was stirred in a mixture of EtOAc/saturated aqueous NaHCO3 solution (2:1) until dissolution, and then extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure. Compound 13 was obtained as a white powder in 99% yield after trituration of the crude product in MeOH and filtration; 1H-NMR (300 MHz; DMSO-d6): δ 12.07 (bs, 1H), 8.57-8.45 (m, 2H), 8.47 (dd, 1H, J=1.5, 4.9 Hz), 7.85 (dd, 1H, J=1.7, 8.5 Hz), 7.57 (d, 1H, J=8.5 Hz), 7.28 (dd, 1H, J=5.0, 7.7 Hz), 7.08 (s, 1H); 13C-NMR (75 MHz; DMSO-d6): δ 170.1 (C), 150.9 (C), 145.1 (CH), 140.3 (C), 139.2 (C), 130.0 (CH), 125.0 (CH), 121.1 (C), 120.4 (C), 119.2 (CH), 116.0 (C), 115.6 (CH), 112.0 (CH), 100.7 (CH); MS (ESI) m/z 267.1 [M+H+]; HRMS (ESI): Calcd for C14H10N4S: 267.0704. Found: 267.0703

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated to dryness
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-89a85c7bcd0943d2854957dd083872c6
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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