Morpholine → HCID 49833716, compound

HRID 1947527Notes

Reaction equation

HRID 1947527 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[C:10]([O:12][C:13]3[S:14][C:15]4[C:16]([N:21]=3)=[N:17][CH:18]=[CH:19][CH:20]=4)[CH:9]=[CH:8][C:6]=2[CH:7]=1.CCN(C(C)C)C(C)C.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CC#N>[N:31]1([CH2:2][C:3]2[O:4][C:5]3[CH:11]=[C:10]([O:12][C:13]4[S:14][C:15]5[C:16]([N:21]=4)=[N:17][CH:18]=[CH:19][CH:20]=5)[CH:9]=[CH:8][C:6]=3[CH:7]=2)[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 59577663HCID 59577663, compound

Product 1

HCID 49833716HCID 49833716, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution 2-(2-chloromethyl-benzofuran-6-yloxy)-thiazolo[4,5-b]pyridine (110 mg, 0.3 mmol) in MeCN (3 mL) was added DIEA (209 μL, 0.155 mg, 0.8 mmol) followed by morpholine (27 μL, 27 mg, 0.3 mmol) and stirred (rt, 12 h). The reaction mixture was partitioned between DCM (15 mL) and saturated NaHCO3 (5 mL). The organic layer was washed with saturated NH4Cl (10 mL), dried, filtered and concentrated in vacuo. The resulting residue was purified by reverse phase chromatography to provide the title compound as colorless crystals (41 mg, 37%). MS (ESI): mass calcd. for C19H17N3O3S, 367.1; m/z found, 368.1.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.56 (dd, J=4.8, 1.7, 1H), 8.01 (dd, J=7.9, 1.7, 1H), 7.59-7.51 (m, 2H), 7.28-7.25 (m, 1H), 7.20 (dd, J=8.0, 4.8, 1H), 6.65 (s, 1H), 3.75 (dd, J=15.5, 10.8, 4H), 3.70 (s, 2H), 2.62-2.49 (m, 4H).

Workup

  1. customThe reaction mixture was partitioned between DCM (15 mL) and saturated NaHCO3 (5 mL)
  2. washThe organic layer was washed with saturated NH4Cl (10 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-5d5357f640954fbba73f9bd8cac65fb6
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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