Diisopropylethylamine → HCID 86691625, compound

HRID 624317Notes

Reaction equation

HRID 624317 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[C:17]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:16][C:11]=3[C:12]=2[C:13]([OH:15])=O)=[CH:4][CH:3]=1.[NH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[C:17]([O:23][CH:24]([CH3:25])[CH3:26])=[CH:16][C:11]=3[C:12]=2[C:13]([NH:27][CH2:28][CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:15])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 187201N-BOC-ethylenediamineHCID 59275582HCID 59275582, compound

Product 1

HCID 86691625HCID 86691625, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-(4-fluorophenyl)-5-isopropoxy-6-nitrobenzofuran-3-carboxylic acid (1.3 g, 3.62 mmol), tert-butyl (2-aminoethyl)carbamate (0.696 g, 4.34 mmol) in DMF (50 mL) at room temperature was added N,N-diisopropylethylamine (DIPEA) (2.53 mL, 14.47 mmol). The mixture was cooled to 0° C., added with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) (2.40 g, 5.43 mmol), and then stirred at room temperature (rt) overnight. The reaction mixture was diluted with water, stirred for 5 min. The solid was filtered and dried under suction to obtain the title compound as a yellow solid. Yield: 1.6 g, (88%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.61 (t, J=5.65 Hz, 1H) 8.32 (s, 1H) 7.90-8.09 (m, 2H) 7.50 (s, 1H) 7.28-7.46 (m, 2H) 6.91 (t, J=5.65 Hz, 1H) 4.87 (dt, J=12.17, 5.96 Hz, 1H) 3.35-3.49 (m, 2H) 3.06-3.23 (m, 2H) 1.09-1.47 (m, 15H). LCMS: (ES+) m/z=502.34 (M+H)+; Column—ACQUITY UPLC BEH C8 (50×2.1 mm; 1.7 nm); M phase A: 5 mM Ammonium Acetate: MeCN (95:5); M phase B: 5 mM Ammonium Acetate:MeCN (5:95)

Workup

  1. stirringstirred for 5 min
  2. filtrationThe solid was filtered
  3. customdried under suction

Sources & evidence

ORD record
ord-5d30fdd03b35429e9d48a4a9735d3e29
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

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