Ethanol → HCID 86710680, compound

HRID 1027266Notes

Reaction equation

HRID 1027266 reaction equation
C(O)C.[CH3:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][C:12]2=O)=[CH:8][C:7]=1[C:16]1[N:17]=[N:18][C:19]([N:22]([CH3:33])[CH:23]2[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]2)=[CH:20][CH:21]=1.[NH2:34][C:35]([NH2:37])=[S:36].II>CO>[CH3:4][O:5][C:6]1[C:7]([C:16]2[N:17]=[N:18][C:19]([N:22]([CH3:33])[CH:23]3[CH2:24][C:25]([CH3:32])([CH3:31])[NH:26][C:27]([CH3:30])([CH3:29])[CH2:28]3)=[CH:20][CH:21]=2)=[CH:8][C:9]2[CH2:10][C:11]3[S:36][C:35]([NH2:37])=[N:34][C:12]=3[C:13]=2[CH:14]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 807IodineHCID 2723790ThioureaHCID 86710623HCID 86710623, compound2×

Product 1

HCID 86710680HCID 86710680, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a microwave vial containing ethanol (1.2 mL) was added 6-methoxy-5-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-2,3-dihydro-1H-inden-1-one (Intermediate 7-1, 100 mg, 0.25 mmol), thiourea (55.9 mL, 0.73 mmol), and iodine (124 mg, 0.49 mmol). The reaction mixture was stirred at 100° C. for 3 hours. The mixture was diluted with MeOH and loaded onto an SCX column. The crude material was washed with methanol then eluted with 2 N ammonia in methanol. The product-containing fractions were concentrated to afford 5-methoxy-6-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-8H-indeno[1,2-d]thiazol-2-amine (114 mg) MS [M+H+]=465.0.

Workup

  1. washThe crude material was washed with methanol
  2. washthen eluted with 2 N ammonia in methanol
  3. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-ca5ac92cdc2a4e488443587ad2c166c1
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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