Dichloromethane → HCID 131728068, compound

HRID 644027Notes

Reaction equation

HRID 644027 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19]3[N:23]=[C:22]([CH2:24]OS(C)(=O)=O)[S:21][N:20]=3)=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31].[Cl:35]CCl>O1CCCC1>[ClH:35].[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19]3[N:23]=[C:22]([CH2:24][N:32]([CH2:33][CH3:34])[CH2:30][CH3:31])[S:21][N:20]=3)=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 86613198HCID 86613198, compound

Product 1

HCID 131728068HCID 131728068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methanesulfonic acid 3-(1-cyclohexylmethyl-7-methoxy-1H-indol-3-yl)-[1,2,4]thiadiazol-5-ylmethyl ester (93 mg, 0.2 mmol) in tetrahydrofuran (1 ml) was added diethylamine (0.22 ml, 2.13 mmol) and the reaction subjected to microwave irradiation at 150° C. for 15 minutes. The reaction was poured into a separating funnel and diluted with dichloromethane (40 ml). The combined organics were washed with 5% aqueous sodium carbonate solution (2×20 ml), brine (2×20 ml), dried over magnesium sulfate and the solvent removed in vacuo. The resulting residue was purified by flash column chromatography to afford the title compound (54 mg, 0.13 mmol) as the free base. The free base was dissolved in dichloromethane and hydrogen chloride (2M solution in diethyl ether; 1.0 ml, 2.0 mmol) was added. The mixture was concentrated in vacuo to afford the title compound as a 1:1 hydrochloride salt. 1H NMR (400 MHz, CD3OD): 0.95-1.12 (2H, m), 1.16-1.27 (3H, m), 1.45 (6H, t, J 7), 1.55-1.63 (2H, m), 1.63-1.8 (3H, m), 1.8-1.95 (1H, m), 3.28-3.32 (4H, m), 3.97 (3H, s), 4.3 (2H, d, J 7), 4.96 (2H, s), 6.79 (1H, d, J 8), 7.13 (1H, t, J 8), 7.95 (1H, s), 8.04 (1H, d, J 8); EsIMS: m/z 413.1 [M+H]+.

Workup

  1. customirradiation at 150° C. for 15 minutes
  2. additionThe reaction was poured into a separating funnel
  3. washThe combined organics were washed with 5% aqueous sodium carbonate solution (2×20 ml), brine (2×20 ml)
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed in vacuo
  6. customThe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-adc2bbf11f24444c962d77c575125122
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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