Diethylcarbamoyl chloride → HCID 57833317, compound

HRID 729971Notes

Reaction equation

HRID 729971 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:20]=[C:19]([NH2:29])[N:18]=3)=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[CH2:30]([N:32]([CH2:36][CH3:37])[C:33](Cl)=[O:34])[CH3:31]>C1COCC1>[NH2:29][C:19]1[N:18]=[C:17]([NH:16][C:13]2[CH:12]=[CH:11][C:10]([O:9][C:7]3[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][NH:1][C:33](=[O:34])[N:32]([CH2:36][CH3:37])[CH2:30][CH3:31])[CH:8]=3)=[CH:15][CH:14]=2)[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:20]=1

Participants

4

Reactant 2

HCID 6916Diethylcarbamoyl chlorideHCID 57833404HCID 57833404, compound

Product 1

HCID 57833317HCID 57833317, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N4-(4-{[2-(Aminomethyl)pyridin-4-yl]oxy} phenyl)-6-phenylpyrimidine-2,4-diamine (50 mg, 0.13 mmol, Example 39) and diethylcarbamyl chloride (20.6 mg, 0.13 mmol) were suspended in THF (1 mL) and stirred at rt for 24 h. TLC and LC-MS indicated that the reaction was complete. The mixture was extracted with EtOAc and washed with 1N aqueous sodium hydroxide solution (2×) and H2O (3×). The organic layer was dried and concentrated to give 72 mg of the crude product. The residue was purified by Prep-TLC (CH3OH:EtOAc=2:8) to obtain 40 mg (63%) of the title product as a yellowish oil. 1H NMR (CD3OD) δ 8.28 (d, 1H), 7.84 (m, 3H), 7.81 (s, 1H), 7.48 (m, 3H), 7.05 (d, 2H), 6.84 (m, 1H), 6.75 (s, 1H), 6.44 (s, 1H), 4.39 (s, 2H), 3.23 (m, 4H), 1.20 (t, 6H); MS ES 484 (M+H)+, calcd 484, RT=2.37 min; TLC (MeOH/EtOAc=20/80) Rf=0.4

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with 1N aqueous sodium hydroxide solution (2×) and H2O (3×)
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give 72 mg of the crude product
  6. customThe residue was purified by Prep-TLC (CH3OH:EtOAc=2:8)

Sources & evidence

ORD record
ord-411a0acacb774bd787ca2eb7eea9cace
Source dataset
uspto-grants-2009_09
Patent number
US07582646B2

Reaction notes

Loading…