Tetrahydrofuran → HCID 67315153, compound

HRID 1012836Notes

Reaction equation

HRID 1012836 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]=[C:10]=[O:11].[ClH:12].Cl.[NH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[C:30]2[O:29][C:28]([C:31]([NH:33][C@@H:34]3[CH:39]4[CH2:40][CH2:41][N:36]([CH2:37][CH2:38]4)[CH2:35]3)=[O:32])=[CH:27][C:26]=2[CH:25]=[CH:24][CH:23]=1.C1COCC1>CN(C=O)C>[ClH:12].[N:36]12[CH2:37][CH2:38][CH:39]([CH2:40][CH2:41]1)[C@@H:34]([NH:33][C:31]([C:28]1[O:29][C:30]3[C:22]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[CH2:15][NH:14][C:10]([NH:9][CH3:8])=[O:11])=[CH:23][CH:24]=[CH:25][C:26]=3[CH:27]=1)=[O:32])[CH2:35]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 67313920HCID 67313920, compound

Product 1

HCID 67315153HCID 67315153, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

62.2 μl (0.45 mmol) of triethylamine and 53 μl (0.89 mmol) of methyl isocyanate are added to a solution of 100 mg (0.22 mmol) of 7-[2-(aminomethyl)phenyl]-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-2-carboxamide dihydrochloride (Example 152) in 1 ml of a 5:1 mixture of THF and DMF. After 18 h at room temperature, the reaction mixture is concentrated and purified by preparative HPLC. The product fractions are concentrated and, after addition of a 3:1 mixture of methanol and 1N hydrochloric acid, again concentrated and dried under high vacuum. 75 mg (66% of theory) of the title compound are obtained.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. custompurified by preparative HPLC
  3. concentrationThe product fractions are concentrated
  4. additionafter addition of a 3:1 mixture of methanol and 1N hydrochloric acid
  5. concentrationagain concentrated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-c6cb0d573e5241939a8414864c27d3f9
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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