Ammonia methanol → HCID 86668012, compound

HRID 474038Notes

Reaction equation

HRID 474038 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2([CH3:15])[NH:13][C:12](=S)[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[NH3:16].CO>>[Br:1][C:2]1[N:7]=[C:6]([C:8]2([CH3:15])[CH2:9][O:10][CH2:11][C:12]([NH2:16])=[N:13]2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 866680135-(6-Bromo-pyridin-2-yl)-5-methyl-morpholine-3-thione

Product 1

HCID 86668012HCID 86668012, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 5-(6-bromo-pyridin-2-yl)-5-methyl-morpholine-3-thione (1.4 g, 4.88 mmol) in 7N NH3/MeOH (20.89 ml, 146 mmol) was stirred at 50° C. for 3 d in an autoclave. The reaction mixture was evaporated to dryness and purified by FC (gradient cyclohexane:EtOAc 75:25 to 50:50, then +10% Et3N, finally MeOH+10% Et3N) to obtain the crude title compound that was further purified by washing with DCM. HPLC RtH4=0.54 min; ESIMS: 270, 272 [(M+H)+]; 1H NMR (400 MHz, DMSO-d6): δ 8.51 (br s, 2H), 7.83-7.79 (m, 1H), 7.63-7.61 (m, 2H), 4.45 (s, 2H), 4.11 (d, 1H), 3.84 (d, 1H), 1.51 (s, 3H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by FC (gradient cyclohexane:EtOAc 75:25 to 50:50

Sources & evidence

ORD record
ord-bd8d6a23e7cf406393a63e21d29a804d
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

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