Cyclopropylamine → HCID 86652728, compound

HRID 1895913Notes

Reaction equation

HRID 1895913 reaction equation
[F:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([O:19][NH:20][C:21](=[O:25])[C:22](O)=[O:23])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH:28]1([NH2:31])[CH2:30][CH2:29]1>CN(C)C=O>[CH:28]1([NH:31][C:22](=[O:23])[C:21]([NH:20][O:19][CH:16]2[CH2:15][CH2:14][N:13]([S:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:26])([F:27])[F:1])=[CH:9][CH:8]=3)(=[O:12])=[O:11])[CH2:18][CH2:17]2)=[O:25])[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 86652727HCID 86652727, compound

Product 1

HCID 86652728HCID 86652728, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (70 mg, 0.37 mmol) was added to a solution of N-[1-(4-trifluoromethoxybenzenesulfonyl)piperidin-4-yloxy]oxalamic acid (102 mg, 0.247 mmol) 1-hydroxybenzotriazole (36 mg, 0.27 mmol) and cyclopropylamine (0.042 ml, 0.61 mmol) in N,N-dimethylformamide (5 ml). The reaction mixture was stirred at room temperature for 16 hours and quenched with aqueous 1 N HCl solution (5 ml) and H2O (5 ml). The resulting precipitation was collected and washed with H2O and diethyl ether to give N1-cyclopropyl-N2-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yloxy)oxalamide (48 mg, 43%) as a white solid: LCMS: 452 [M+1]+. 1H NMR (DMSO-d6) δ: 0.59 (m, 4H), 1.69 (m, 2H), 1.82 (m, 2H), 2.73 (m, 1H), 3.04 (m, 4H), 3.96 (m, 1H), 7.65 (d, 2H), 7.88 (d, 2H), 8.81 (d, 1H), 11.9 (s, 1H).

Workup

  1. customquenched with aqueous 1 N HCl solution (5 ml) and H2O (5 ml)
  2. customThe resulting precipitation
  3. customwas collected
  4. washwashed with H2O and diethyl ether

Sources & evidence

ORD record
ord-a3a8faf0d403465b97799fdd499f249b
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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