Dichloromethane → HCID 66893894, compound

HRID 1161978Notes

Reaction equation

HRID 1161978 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][CH2:12][N:13]([CH3:33])[C:14]1[C:22]2[O:21][CH:20]=[CH:19][C:18]=2[CH:17]=[C:16]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:15]=1)C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:42]>>[ClH:42].[CH3:33][N:13]([CH2:12][CH2:11][CH2:10][NH:2][CH3:1])[C:14]1[C:22]2[O:21][CH:20]=[CH:19][C:18]=2[CH:17]=[C:16]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:15]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 69626822HCID 69626822, compound2×

Product 1

HCID 66893894HCID 66893894, compoundYield 98%

Procedure

tert-Butyl methyl[3-(methyl{5-[(phenylsulfonyl)amino]-1-benzofuran-7-yl}amino)propyl]carbamate (Intermediate 3; 202 mg, 0.43 mmol) in DCM (2 mL) was treated with TFA (2 mL) at 0° C. for 10 min and was stirred for an additional 30 min at room temperature. After concentration in vacuo, the residue was re-dissolved in MeOH and treated with an excess of 1M HCl in diethyl ether. Removal of the solvents gave the title compound (173 mg, 98%) as a white solid; HPLC 100%, RT: 1.65 min (System A); 100%, RT: 0.630 min (System B); 1H NMR (methanol-d4) δ ppm 1.85-2.00 (m, 2H), 2.67 (s, 3H), 3.04-3.17 (m, 5H), 3.64-3.73 (m, 2H), 6.81-6.84 (m, 1H), 6.95-6.98 (m, 1H), 7.06-7.09 (m, 1H), 7.43-7.60 (m, 3H), 7.72-7.78 (m, 2H), 7.81-7.85 (m, 1H); MS m/z 374 (M+H)+.

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue was re-dissolved in MeOH
  3. additiontreated with an excess of 1M HCl in diethyl ether
  4. customRemoval of the solvents

Sources & evidence

ORD record
ord-c815448e3a6d4af69446ea5bc9e975d3
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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