m-Tolyl isocyanate → HCID 71736174, compound

HRID 338761Notes

Reaction equation

HRID 338761 reaction equation
Cl.Cl.Cl.[CH2:4]1[C:13]2[C:8](=[CH:9][CH:10]=[N:11][CH:12]=2)[CH2:7][CH2:6][N:5]1[C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([CH3:21])[CH:15]=1.C(N(CC)C(C)C)(C)C.[C:31]1([CH3:40])[CH:36]=[CH:35][CH:34]=[C:33]([N:37]=[C:38]=[O:39])[CH:32]=1>C(Cl)Cl>[CH2:4]1[C:13]2[C:8](=[CH:9][CH:10]=[N:11][CH:12]=2)[CH2:7][CH2:6][N:5]1[C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:38]([NH:37][C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([CH3:40])[CH:32]=2)=[O:39])=[C:16]([CH3:21])[CH:15]=1

Participants

5

Reactant 3

HCID 69303m-Tolyl isocyanateHCID 81531DiisopropylethylamineHCID 86695875HCID 86695875, compound

Product 1

HCID 71736174HCID 71736174, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(3,4-dihydro-2,7-naphthyridin-2(1H)-yl)-2-methylaniline trihydrochloride (35 mg, 0.10 mmol) and N,N-diisopropylethylamine (0.061 mL, 0.35 mmol) in 1.5 mL CH2Cl2 at rt was added meta-tolyl isocyanate (0.019 mL, 0.15 mmol) and the reaction stirred at rt for 3 hours. The reaction was quenched into a brine/aqueous Na2CO3 solution, then extracted with EtOAc. The EtOAc layer was washed with brine/aqueous Na2CO3 solution, dried with anhydrous Na2SO4, and evaporated to a solid. The solid was triturated with EtOAc and then with 20% CHCl3/EtOAc to give the title compound as a beige solid (21 mg, 56%). 1H NMR (Acetone-d6) δ: 8.44 (s, 1H), 8.31 (d, J=5.0 Hz, 1H), 8.07 (s, 1H), 7.56-7.61 (m, 1H), 7.35-7.38 (m, 1H), 7.26-7.34 (m, 2H), 7.08-7.16 (m, 2H), 6.92-6.95 (m, 1H), 6.87-6.92 (m, 1H), 6.75-6.80 (m, 1H), 4.39 (s, 2H), 3.55 (t, J=5.9 Hz, 2H), 2.98 (td, J=5.9, 0.9 Hz, 2H), 2.27 (s, 3H), 2.26 (s, 3H)

Workup

  1. customThe reaction was quenched into a brine/aqueous Na2CO3 solution
  2. extractionextracted with EtOAc
  3. washThe EtOAc layer was washed with brine/aqueous Na2CO3 solution
  4. dry with materialdried with anhydrous Na2SO4
  5. customevaporated to a solid
  6. customThe solid was triturated with EtOAc

Sources & evidence

ORD record
ord-0cce2553b511498dbe3c7be1a14fcb33
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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