Dimethylacetamide → HCID 178467439, compound

HRID 1364569Notes

Reaction equation

HRID 1364569 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.F[B-](F)(F)F.N1(O[C:31]([N:35]([CH3:37])C)=[N+:32]([CH3:34])C)C2C=CC=CC=2N=N1.[CH:38]([N:41](C(C)C)CC)(C)C.[CH3:47]N(C)C(=O)C>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:41][CH2:38][C:31]2[NH:32][CH:34]=[C:37]([CH3:47])[N:35]=2)=[O:15])[CH:3]=1

Participants

5

Reactant 4

HCID 31374Dimethylacetamide4×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118464604-Amino-5-cyano-6-ethoxypicolinic acid

Product 1

HCID 178467439HCID 178467439, compound

Procedure

In a 20 mL vial a solution of Example 104A (32.5 mg, 0.16 mmol) dissolved in N,N-dimethylacetamide (0.8 mL) was added, followed by the addition of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (50.4 mg, 0.16 mmol) dissolved in N,N-dimethylacetamide (0.8 mL). Then, c-(4-Methyl-1H-imidazol-2-yl)-methylamine hydrochloride (21.1 mg, 0.19 mmol) dissolved in N,N-dimethylacetamide (0.6 mL) was added followed by the addition of diisopropyl ethyl amine (57.9 uL, 0.31 mmol) dissolved in N,N-dimethylacetamide (0.8 mL). The mixture was shaken at room temperature overnight. The reaction was checked by LC/MS and concentrated to dryness. The residue was dissolved in 1:1 dimethyl sulfoxide/methanol and purified by reverse phase (0-70% CH3CN in 10 mM aq. ammonium acetate) to give the titled compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.08-1.48 (m, 3H) 1.88-2.28 (m, 2H) 4.28-4.46 (m, 2H) 4.47-4.58 (m, 2H) 6.32-6.82 (m, 1H) 6.90-7.21 (m, 1H); MS (ESI) positive ion 301 (M+H).

Workup

  1. additionwas added
  2. additionwas added
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was dissolved in 1:1 dimethyl sulfoxide/methanol
  5. custompurified by reverse phase (0-70% CH3CN in 10 mM aq. ammonium acetate)

Sources & evidence

ORD record
ord-f523cdd12f554d6cb78b108f63ee5ac3
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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