Water → HCID 86686154, compound

HRID 1409695Notes

Reaction equation

HRID 1409695 reaction equation
[CH:1]1([N:4]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=3)=[N:8][CH:7]=2)[CH2:3][CH2:2]1.[CH2:29]([N:31](C(C)C)C(C)C)C.O.C(OCC)(=O)C>ClCCl.O1CCCC1>[C:29]([N:26]1[CH2:27][CH2:28][CH:23]([N:4]([CH:1]2[CH2:3][CH2:2]2)[C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[CH:14][C:15]([S:18]([CH3:21])(=[O:19])=[O:20])=[CH:16][CH:17]=3)=[N:8][CH:7]=2)[CH2:24][CH2:25]1)#[N:31]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 71093778HCID 71093778, compound

Product 1

HCID 86686154HCID 86686154, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Bromonitrile (44 mg) is added to a solution of N-cyclopropyl-6-(4-methanesulfonyl-phenyl)-N-piperidin-4-yl-nicotinamide (111 mg) and ethyldiisopropylamine (238 μL) in dichloromethane (2.5 mL) and tetrahydrofuran (2.5 mL). The reaction mixture is stirred for two days at room temperature prior to the addition of water and ethyl acetate. The organic phase is separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The crude product is used without further purification for the next reaction step. LC (method 7): tR=0.87 min; Mass spectrum (ESI+): m/z=425 [M+H]+.

Workup

  1. customThe organic phase is separated
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is used without further purification for the next reaction step

Sources & evidence

ORD record
ord-ae766adaf2e649079b405e132f5d3044
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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