Dichloromethane → HCID 131728078, compound

HRID 644083Notes

Reaction equation

HRID 644083 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[N:10]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:9]=[C:8]2[C:19]1[N:23]=[C:22]([CH2:24]OS(C)(=O)=O)[S:21][N:20]=1)#[N:2].[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.C(OCC)(=O)C.[Cl:41]CCl>CCCCCCC>[ClH:41].[CH:13]1([CH2:12][N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[CH:4][C:3]=3[C:1]#[N:2])[C:8]([C:19]3[N:23]=[C:22]([CH2:24][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[S:21][N:20]=3)=[CH:9]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 86613201HCID 86613201, compound

Product 1

HCID 131728078HCID 131728078, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

To a solution of methanesulfonic acid 3-(7-cyano-1-cyclohexylmethyl-1H-indol-3-yl)-[1,2,4]thiadiazol-5-ylmethyl ester (120 mg, 0.28 mmol) in dichloromethane (3 ml) was added pyrrolidine (0.12 ml, 1.4 mmol) and the reaction subjected to microwave irradiation at 100° C. for 5 minutes. The reaction was purified directly by flash column chromatography eluting with dichloromethane then 25-50% (v/v) ethyl acetate in heptane to afford the title compound (71 mg, 0.175 mmol) as the free base. The free base (35 mg, 0.086 mmol) was dissolved in dichloromethane (2 ml) and hydrogen chloride (1M solution in diethyl ether) was added. The mixture was concentrated in vacuo to afford the title compound as a 1:1 hydrochloride salt. 1H NMR (400 MHz, CD3OD): 1.06-1.36 (7H, m), 1.62-1.80 (5H, m), 1.91-2.07 (1H, m), 2.09-2.34 (2H, br m), 3.35-4.20 (4H, br m), 4.42 (2H, d, J 7), 5.07 (2H, s), 7.37 (1H, t, J 8), 7.69 (1H, dd, J 7, 1), 8.23 (1H, s); 8.84 (1H, dd, J 8, 1) EsIMS: m/z 406.4 [M+H]+.

Workup

  1. customirradiation at 100° C. for 5 minutes
  2. customThe reaction was purified directly by flash column chromatography
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-be387f72dcd34779812a70f995177c0d
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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