Water → HCID 49784700, compound

HRID 1184368Notes

Reaction equation

HRID 1184368 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])=[C:7]([S:9](Cl)(=[O:11])=[O:10])[CH:8]=1)#[N:2].[CH3:22][N:23]([CH3:30])[CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.CCOC(C)=O.O>C(Cl)Cl>[F:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[O:13][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][C:7]=1[S:9]([N:27]1[CH2:28][CH2:29][CH:24]([N:23]([CH3:30])[CH3:22])[CH2:25][CH2:26]1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 417391N,N-Dimethylpiperidin-4-amineHCID 59548931HCID 59548931, compound

Product 1

HCID 49784700HCID 49784700, compoundYield 840.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 23 (0.080 g, 0.24 mmol) in DCM (10.00 mL) was added 4-dimethylaminopiperidine (0.040 g, 0.31 mmol) and TEA (0.043 g, 0.31 mmol). The reaction was monitored with TLC (25% EtOAc in hexanes, Rf=0.0). The reaction was complete after stirring at room temperature for 30 min, as indicated by the absence of the starting material (TLC). Water was then added and extracted twice with DCM. Combined organic extracts were washed sequentially with water and brine, dried over MgSO4, filtered, and evaporated in vacuo to form a yellow oil. The oil was triturated with DCM and hexanes, and filtered to yield compound 59 as a white powder (0.85 g, 97.4% HPLC purity, 84% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.27 (d, J=2 Hz, 1H), 8.08 (dd, J1=2 Hz, J2=8 Hz, 1H), 7.56 (m, 1H), 7.40 (m, 1H), 7.26 (m, 1H), 7.19 (d, J=9 Hz, 1H), 3.71 (d, J=13 Hz, 2H), 2.77 (t, J=13 Hz, 2H), 2.18 (m, 1H), 2.12 (s, 3H), 1.76 (d, J=11 Hz, 2H), 1.35 (m, 2H); MS (ESI, EI+): m/z=422 (MH+); melting point: 154-157° C.

Workup

  1. extractionextracted twice with DCM
  2. washCombined organic extracts were washed sequentially with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto form a yellow oil
  7. customThe oil was triturated with DCM and hexanes
  8. filtrationfiltered

Sources & evidence

ORD record
ord-4b73e5866a2044718e329bfa725a1cbe
Source dataset
uspto-grants-2014_03
Patent number
US08669247B2

Reaction notes

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