tert-Butyl isocyanate → HCID 118069148, compound

HRID 920712Notes

Reaction equation

HRID 920712 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]([NH2:19])=[O:18])=[C:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:20]([N:24]=[C:25]=[O:26])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[C:20]([NH:24][C:25]([N:13]1[CH2:14][CH2:15][N:10]2[N:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[C:16]([C:17]([NH2:19])=[O:18])=[C:11]2[CH2:12]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 118061505HCID 118061505, compound

Product 1

HCID 118069148HCID 118069148, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Intermediate 1K (30 mg, 0.115 mmol) in DMF (1 mL) was added tert-butylisocyanate (28.6 mg, 0.288 mmol) at 0° C. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with water and extracted with ethyl acetate (3×5 mL). The combined organic layer was washed with water (2×5 mL), brine, dried over Na2SO4 and concentrated to afford the crude product as brown semi-solid. The residue was dissolved in a mixture of acetonitrile and methanol and was purified via preparative HPLC. Fractions containing the desired product (0.01 g, 24%) were combined and dried under vacuum. MS(ES): m/z=360 [M+H]+; HPLC Ret. Time 6.66 min. and 6.14 min. (HPLC Methods A and B); 1H NMR (400 MHz, DMSO-d6) δ ppm 7.69 (m, 2H), 7.25 (m, 2H), 7.25 (bs, 1H), 6.98 (bs, 1H), 6.26 (s, 1H), 4.69 (s, 2H), 4.11 (t, J=5.7 Hz, 2H), 3.80 (t, J=5.7 Hz, 2H), 1.29 (s, 9H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (3×5 mL)
  3. washThe combined organic layer was washed with water (2×5 mL), brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4ac77c790f3f46a0a89e474691a32afa
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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