1,1-Dichloroethane → HCID 18382845, compound

HRID 2297833Notes

Reaction equation

HRID 2297833 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][C:13]([C:16]([OH:19])([CH3:18])[CH3:17])=[CH:14][N:15]=3)[S:10][C:3]=12.[CH3:20][C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([NH2:30])=[CH:25][CH:24]=2.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.ClC(Cl)C>C(O)(C)(C)C>[CH3:20][C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([NH:30][C:2]1[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[S:12][C:13]([C:16]([OH:19])([CH3:18])[CH3:17])=[CH:14][N:15]=4)[S:10][C:3]=13)=[CH:25][CH:24]=2

Participants

7

Reactant 5

HCID 63651,1-DichloroethaneHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 27339925-Amino-2-methylindoleHCID 18383075HCID 18383075, compound

Product 1

HCID 18382845HCID 18382845, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-[2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-thiazol-5-yl]-propan-2-ol (129 mg, 0.42 mmol), 2-methyl-5-aminoindole (72 mg, 0.50 mmol), potassium carbonate (138 mg. 8.84 mmol), and triethylamine (0.12 mL, 0.84 mmol) were dissolved in 2 mL of t-butyl alcohol and 2 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 36 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 (40%) of 2-{2-[7-(2-methyl-1H-indol-5-ylamino)-thieno[3,2-b]pyridin-2-yl]-thiazol-5-yl}-propan-2-ol. 1H NMR (400 MHz, CD3OD) δ8.13 (d, 1H), 7.71 (s, 1H), 7.62 (s, 1H), 7.35 (d, 1H), 7.30 (d, 1H), 6.99 (d, 1H), 6.64 (d, 1H), 6.13 (s, 1H), 2.43 (s, 3H), 1.65 (s, 6H). LC-MS: 421 (MH+); HPLC RT: 4.75 min.

Workup

  1. customthe reaction
  2. customto go dry overnight solvent
  3. additionwas added along with an additional 36 mg of the indole an the solution
  4. temperaturewas heated an additional 18 hours

Sources & evidence

ORD record
ord-c5defe34e4cc4deca0e1582bf77a800b
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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