1,1-Dichloroethane → 2-(1-methyl-5-(7-(2-methyl-1H-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl)-1H-imidazol-2-yl)propan-2-ol

HRID 2297829Notes

Reaction equation

HRID 2297829 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:15]([CH3:16])[C:14]([C:17]([OH:20])([CH3:19])[CH3:18])=[N:13][CH:12]=3)[S:10][C:3]=12.[CH3:21][C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][C:27]([NH2:31])=[CH:26][CH:25]=2.ClC(Cl)C>C(O)(C)(C)C>[CH3:16][N:15]1[C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[NH:31][C:27]3[CH:28]=[C:29]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22]([CH3:21])=[CH:30]4)[CH:8]=2)=[CH:12][N:13]=[C:14]1[C:17]([OH:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 27339925-Amino-2-methylindoleHCID 183828632-(5-(7-chlorothieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-2-yl)propan-2-ol

Product 1

HCID 183830542-(1-methyl-5-(7-(2-methyl-1H-indol-5-ylamino)thieno[3,2-b]pyridin-2-yl)-1H-imidazol-2-yl)propan-2-olYield 66%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-[5-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-2-yl]-propan-2-ol (190 mg, 0.62 mmol) and 2-methyl-5-aminoindole (108 mg, 0.714 mmol) were dissolved in 3 mL of t-butyl alcohol and 3 mL of dichloroethane and the solution was heated to 85° C. After allowing the reaction to go dry overnight solvent was added along with an additional 45 mg of the indole an the solution was heated an additional 18 hours. Chromatography of the residue with 20% methanol:methylene chloride afforded 166 mg (66%) of 2-{1-methyl-5-[7-(2-methyl-1H-indol-5-ylamino)-thieno[3,2-b]pyridin-2-yl]-1H-imidazol-2-yl}-propan-2-ol. 1H NMR (400 MHz, CD3OD) δ8.17 (d, 1H), 7.51 (s, 1H), 7.44 (s, 1H), 7.40 (d, 1H), 7.02 (d, 1H), 6.84 (s, 1H), 6.20 (s, 1H), 3.33 (s, 3H), 2.44 (s, 3H), 1.64 (s, 6H). LC-MS: 418, 419 (MH+); HPLC RT: 3.98 min.

Workup

  1. customthe reaction
  2. customto go dry overnight solvent
  3. additionwas added along with an additional 45 mg of the indole an the solution
  4. temperaturewas heated an additional 18 hours

Sources & evidence

ORD record
ord-e3b39dad3198470ea1b8d2bc394a257e
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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