m-Tolyl isocyanate → HCID 71736173, compound

HRID 338759Notes

Reaction equation

HRID 338759 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])=[CH:16][C:15]=1[CH3:21].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])=[CH:16][C:15]=1[CH3:21]

Participants

5

Reactant 3

HCID 69303m-Tolyl isocyanateHCID 81531DiisopropylethylamineHCID 86695872HCID 86695872, compound

Product 1

HCID 71736173HCID 71736173, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(3,4-dihydro-2,7-naphthyridin-2(1H)-yl)-3-methylaniline trihydrochloride (24.7 mg, 0.071 mmol) and N,N-diisopropylethylamine (0.043 mL, 0.25 mmol) in 1.0 mL CH2Cl2 at rt was added meta-tolyl isocyanate (0.013 mL, 0.106 mmol) and the reaction stirred at rt for 1.5 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 an oily solid. The oil was chromatographed eluting with CHCl3/EtOAc plus 0.5% MeOH to give the title compound as a faint yellow solid (26 mg, 97%). 1H NMR (Acetone-d6) δ: 8.35 (s, 1H), 8.32 (d, J=5.0 Hz, 1H), 7.97 (s, 1H), 7.93 (s, 1H), 7.29-7.40 (m, 4H), 7.08-7.17 (m, 3H), 6.80 (d, J=7.3 Hz, 1H), 4.07 (s, 2H), 3.15-3.20 (m, 2H), 2.97-3.03 (m, 2H), 2.30 (s, 3H), 2.29 (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 an oily solid
  6. customThe oil was chromatographed
  7. washeluting with CHCl3/EtOAc plus 0.5% MeOH

Sources & evidence

ORD record
ord-ad47fb3ef53042dfabaa04f3057b42d5
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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