Isobutyl chloroformate → N-(2-Cyanobenzo[d]thiazol-6-yl)-3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide

HRID 921506Notes

Reaction equation

HRID 921506 reaction equation
[CH3:1][C:2]([C:8]1[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[C:10](=[O:17])[C:9]=1[CH3:18])([CH3:7])[CH2:3][C:4]([OH:6])=O.ClC(OCC(C)C)=O.[NH2:27][C:28]1[CH:38]=[CH:37][C:31]2[N:32]=[C:33]([C:35]#[N:36])[S:34][C:30]=2[CH:29]=1>C1COCC1>[C:35]([C:33]1[S:34][C:30]2[CH:29]=[C:28]([NH:27][C:4](=[O:6])[CH2:3][C:2]([CH3:1])([C:8]3[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[C:10](=[O:17])[C:9]=3[CH3:18])[CH3:7])[CH:38]=[CH:37][C:31]=2[N:32]=1)#[N:36]

Participants

5

Reactant 3

HCID 62365Isobutyl chloroformateHCID 141571126-Amino-2-cyanobenzothiazoleHCID 144150783-Methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic Acid

Product 1

HCID 71285597N-(2-Cyanobenzo[d]thiazol-6-yl)-3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamideYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid (0.72 g, 3.09 mmol) and isobutyl chloroformate (0.44 g, 3.24 mmol) in 10 ml of dry THF, N-methyl morphorline (0.34 ml) was added at 0° C. The resultant mixture was stirred for 30 minutes at 0° C., and 6-amino-2-cyanobenzothiazole (0.36 g, 2.06 mmol) added. The resultant mixture was stirred overnight. The compound was directly purified with flash silica column using heptane and ethyl acetate as eluent to give a yield 10%. 1H NMR (300 MHz, CD2Cl2) δ 8.57 (d, J=2.0, 2H), 8.06 (d, J=9.0, 2H), 7.67 (s, 1H), 7.40 (dd, J=2.1, 8.9, 1H), 3.08 (s, 2H, CH2), 2.22 (s, 3H, CH3), 2.22 (s, 3H, CH3), 1.99 (s, 3H, CH3), 1.97 (s, 3H, CH3), 1.50 (s, 6H, CH3). MS (m/e): 408 (M+).

Workup

  1. customThe compound was directly purified with flash silica column
  2. customto give a yield 10%

Sources & evidence

ORD record
ord-17292c3052e4488e9833611216e916af
Source dataset
uspto-grants-2016_03
Patent number
US09273343B2

Reaction notes

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