Diisopropylethylamine → HCID 86590193, compound

HRID 1829993Notes

Reaction equation

HRID 1829993 reaction equation
FC1C(O[C:9]([C:11]2[N:12]([CH2:19][CH:20]3[CH2:22][CH2:21]3)[CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=2)=[O:10])=C(F)C(F)=C(F)C=1F.S(=O)(=O)(O)O.[NH2:32][CH2:33][C:34]#[N:35].C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:33]([CH2:34][NH:35][C:9]([C:11]1[N:12]([CH2:19][CH:20]2[CH2:21][CH2:22]2)[CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1)=[O:10])#[N:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 196971Aminoacetonitrile sulfate (1:1)HCID 86590192HCID 86590192, compound

Product 1

HCID 86590193HCID 86590193, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of compound 278 (3.6 g, 9.57 mmol), aminoacetonitrile bisulfate (2.94 g, 19.12 mmol) and N,N-diisopropylethyl-amine (3.5 ml) in DMF (60 ml) was stirred under Ar at 55° C. for 16 h. After evaporation of solvent, the residue was separated by chromatography on silica gel eluted by CHCl3-ethyl acetate (10:1) to give g of compound 279. MS (ESI) 247.12 (M−H+). H1-NMR (DMSO-d6) 9.16 (t, 1H), 8.26 ((d, 1H), 7.49 (d, 1H), 4.28 (d, 2H), 4.23 (d, 2H), 1.30–1.28 (m, 1H), 0.50–0.46 (m, 2H), 0.41−0.38 (m, 2H).

Workup

  1. customAfter evaporation of solvent
  2. customthe residue was separated by chromatography on silica gel
  3. washeluted by CHCl3-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-2d4d16d6f6af448e8beadb3d24fa009d
Source dataset
uspto-grants-2006_06
Patent number
US07064218B2

Reaction notes

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