Morpholine → HCID 59447962, compound

HRID 1916302Notes

Reaction equation

HRID 1916302 reaction equation
Cl[C:2]1[C:3]2[C:10]3[CH:11]=[CH:12][N:13]=[CH:14][C:9]=3[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(N(CC)CC)C>CN1C(=O)CCC1>[N:15]1([C:2]2[C:3]3[C:10]4[CH:11]=[CH:12][N:13]=[CH:14][C:9]=4[NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 59447945HCID 59447945, compound

Product 1

HCID 59447962HCID 59447962, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-chloro-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidine (18 mg, 0.09 mmol), morpholine (23 μL, 0.26 mmol) and triethylamine (62 μL, 0.44 mmol) in 1 mL of NMP was irradiated in a microwave reactor at 150° C. for 20 minutes. The reaction mixture was evaporated to dryness and the residue purified by prep HPLC to give 7.6 mg of a white solid. 1H NMR (DMSO, 6, ppm) δ 3.65-3.75 (8H, m), 7.70 (1H, d, J=5.5 Hz), 8.45 (1H, d, J=5.5 Hz), 8.55 (1H, s), 8.85 (1H, s), 12.50 (1H, br s); LC-MS (2) Rt 1.46 min; m/z (ES+) 256.

Workup

  1. customwas irradiated in a microwave reactor at 150° C. for 20 minutes
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue purified by prep HPLC

Sources & evidence

ORD record
ord-84fa723797be423997bc48ba1e6fafd2
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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