Diisopropylethylamine → HCID 66760573, compound

HRID 389495Notes

Reaction equation

HRID 389495 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([C:11]3[O:31][C:14]4=[C:15]([NH2:30])[N:16]=[CH:17][C:18]([C:19]5[CH:20]=[N:21][N:22]([CH:24]6[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]6)[CH:23]=5)=[C:13]4[CH:12]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[CH3:32][O:33][CH2:34][C:35](Cl)=[O:36].CCN(C(C)C)C(C)C>C(Cl)Cl>[NH2:30][C:15]1[N:16]=[CH:17][C:18]([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:25][CH2:26][N:27]([C:35](=[O:36])[CH2:34][O:33][CH3:32])[CH2:28][CH2:29]3)[CH:23]=2)=[C:13]2[CH:12]=[C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH:4]=[CH:3][N:2]=[CH:1]4)[O:31][C:14]=12

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 53377742HCID 53377742, compound

Product 1

HCID 66760573HCID 66760573, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-isoquinolin-5-yl-4-(1-piperidin-4-yl-1H-pyrazol-4-yl)-furo[2,3-c]pyridin-7-ylamine (30 mg, 0.07 mmol), methoxyacetyl chloride (8.02 μL, 0.0877 mmol), and DIPEA (28.0 μL, 0.161 mmol) in DCM (0.94 mL) stirred overnight at RT. The reaction was diluted with DCM, washed with water and brine, dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (10% 7 N NH3/MeOH:EtOAc) afforded 20 mg (60%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 1.97-2.21 (m, 4 H) 2.31 (br s, 2 H) 2.81-2.94 (m, 1 H) 3.17-3.32 (m, 1 H) 3.41-3.51 (m, 3 H) 4.06-4.25 (m, 3 H) 4.46 (tt, J=11.34, 4.07 Hz, 1 H) 4.76 (d, J=12.88 Hz, 1 H) 5.01 (br s, 2 H) 7.22 (s, 1 H) 7.69-7.80 (m, 2 H) 7.84-7.91 (m, 1 H) 8.03 (s, 1 H) 8.08-8.18 (m, 2 H) 8.22 (d, J=6.06 Hz, 1 H) 8.61-8.70 (m, 1 H) 9.37 (s, 1 H); MS (ESI): 483.11 [M+H]+; HPLC tR=0.89 min (TOF, polar—3 min).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography (10% 7 N NH3/MeOH:EtOAc)

Sources & evidence

ORD record
ord-5a27406f34d147e9bdc47960bafe182e
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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