Water → HCID 57315557, compound

HRID 333884Notes

Reaction equation

HRID 333884 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH:5]1C=CC2N(O)N=NC=2[CH:10]=1.[OH2:15].CCN([CH:22]([CH3:24])[CH3:23])C(C)C.[CH3:25]CN=C=NCCCN(C)C.Cl>C(Cl)Cl.CCOCC>[CH:1]1([NH:4][C:25](=[O:15])[C:22]([CH3:23])([CH3:24])[C:5]#[CH:10])[CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 962WaterHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57315557HCID 57315557, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,1-dimethyl-3-butynoic acid (247 mg, 2.2 mmol), cyclopropylamine (0.23 mL, 3.3 mmol), HOBt.H2O (506 mg, 3.3 mmol) and i-Pr2NEt (1.2 mL, 6.6 mmol) in CH2Cl2 (10 mL) was added EDC.HCl (633 mg, 3.3 mmol). The mixture was stirred at rt for 18 h, diluted with ether (90 mL), washed with 5% aq HCl (15 mL) and satd aq NaHCO3 (15 mL), and dried over Na2SO4. Removal of the solvent left N-cyclopropyl-2,2-dimethylbut-3-ynamide (187 mg, 56%). 1H NMR (CDCl3) 0.53 (m, 2H), 0.79 (m, 2H), 1.44 (s, 6H), 2.45 (s, 1H), 2.73 (m, 1H), 6.76 (br s, 1H).

Workup

  1. washwashed with 5% aq HCl (15 mL)
  2. dry with materialdried over Na2SO4
  3. customRemoval of the solvent
  4. waitleft N-cyclopropyl-2,2-dimethylbut-3-ynamide (187 mg, 56%)

Sources & evidence

ORD record
ord-01336a93642d490ea8c2bb6f9777eaf7
Source dataset
uspto-grants-2014_11
Patent number
US08883778B2

Reaction notes

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