Diisopropylethylamine → HCID 66920760, compound

HRID 1364567Notes

Reaction equation

HRID 1364567 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(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH2:38][CH2:39][C:40]1[S:44][CH:43]=[N:42][CH:41]=1.C(N(C(C)C)CC)(C)C>CN(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:38][CH2:39][C:40]2[S:44][CH:43]=[N:42][CH:41]=2)=[O:15])[CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 53040775-(Aminomethyl)-1,3-thiazoleHCID 118464604-Amino-5-cyano-6-ethoxypicolinic acid

Product 1

HCID 66920760HCID 66920760, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent4×

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, 5-(aminomethyl)thiazole (21.7 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 HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate) to give the titled compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.25-1.39 (m, 3H) 4.43-4.54 (m, 2H) 4.58-4.68 (m, 2H) 7.04-7.14 (m, 1H) 7.37-7.45 (m, 1H) 8.83-9.19 (m, 1H); MS (ESI) positive ion 304 (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 HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate)

Sources & evidence

ORD record
ord-2c7f9e82d48f4bea9289d88484b3f451
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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