1-Hydroxybenzotriazole → HCID 86654286, compound

HRID 450123Notes

Reaction equation

HRID 450123 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:14]2[CH:15]=[N:16][CH:17]=[CH:18][C:13]2=[CH:12][C:11]=1[C:19]([OH:21])=O.[CH:22]([O:24][CH2:25][CH2:26][O:27][NH2:28])=[CH2:23].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:22]([O:24][CH2:25][CH2:26][O:27][NH:28][C:19]([C:11]1[CH:12]=[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]2[C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1])=[O:21])=[CH2:23]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 672358207-(2-Fluoro-4-iodo-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid

Product 1

HCID 86654286HCID 86654286, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(2-Fluoro-4-iodo-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid (67 mg, 0.18 mmol), O-(2-vinyloxy-ethyl)-hydroxylamine (18 mg, 0.18 mmol), HOBt (26 mg, 0.19 mmol), EDCI hydrochloride (37 mg, 0.19 mmol) and DIPEA (31 μL, 0.18 mmol) were suspended in DMF (3 mL). The reaction mixture was stirred at room temperature for 16 hours, during which time the reagents dissolved. The reaction mixture was concentrated in vacuo, the resultant residue dissolved in ethyl acetate (10 mL), washed with aqueous saturated sodium bicarbonate solution (10 mL) and the aqueous fraction extracted twice with ethyl acetate (2×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0-100% ethylacetate in cyclohexane) to yield the title compound as a yellow solid (54 mg, 65%). LCMS (Method B): RT=3.38 min, M+H+=483.

Workup

  1. dissolutiondissolved
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe resultant residue dissolved in ethyl acetate (10 mL)
  4. washwashed with aqueous saturated sodium bicarbonate solution (10 mL)
  5. extractionthe aqueous fraction extracted twice with ethyl acetate (2×10 mL)
  6. washThe combined organic fractions were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3699902e9d3745f9bbfbc71a1824a0b6
Source dataset
uspto-grants-2013_07
Patent number
US08486963B2

Reaction notes

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