Water → (3R)-N-(4'-{[(Methylamino)carbonyl]amino}biphenyl-4-yl)quinuclidine-3-carboxamide

HRID 2362764Notes

Reaction equation

HRID 2362764 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].C(N(CC)CC)C.Cl.Cl.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([C@@H:30]3[CH:35]4[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]4)[CH2:31]3)=[O:29])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.O>CN(C=O)C>[CH3:1][NH:2][C:3]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][C:24]([NH:27][C:28]([C@@H:30]3[CH:35]4[CH2:34][CH2:33][N:32]([CH2:37][CH2:36]4)[CH2:31]3)=[O:29])=[CH:25][CH:26]=2)=[CH:17][CH:16]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 67427707(3R)-N-(4'-Aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride

Product 1

HCID 11485757(3R)-N-(4'-{[(Methylamino)carbonyl]amino}biphenyl-4-yl)quinuclidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17.4 mg (0.30 mmol) of methyl isocyanate and 84.8 μl (0.61 mmol) of triethylamine are added to a solution of 60 mg (0.15 mmol) of ((3R)—N-(4′-aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride (Example 7A) in 0.5 ml of DMF. After 18 h at room temperature, 5 ml of water are added to the reaction mixture. The resulting precipitate is filtered off with suction, washed with water and dried under high vacuum. 47 mg (73.5% of theory) of the title compound are obtained. HPLC (Method 1): Rt=3.44 min. MS (ESIpos): m/z=379 (M+H)+.

Workup

  1. filtrationThe resulting precipitate is filtered off with suction
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-e2d46dd827744c66a132de3a64872b66
Source dataset
uspto-grants-2014_04
Patent number
US08691840B2

Reaction notes

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