Hydrochloric Acid → HCID 42636505, compound

HRID 450124Notes

Reaction equation

HRID 450124 reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]2[C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=1[F:27])=[O:9])=C.Cl>>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]2[C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=1[F:27])=[O:9]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86654286HCID 86654286, compound

Product 1

HCID 42636505HCID 42636505, compoundYield 39.9%

Procedure

To a solution of 7-(2-fluoro-4-iodo-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid (2-vinyloxy-ethoxy)-amide (54 mg, 0.11 mmol) in IMS (3 mL) was added aqueous hydrochloric acid (0.5 mL, 1M, 0.5 mmol). The reaction was stirred at room temperature for 1 hour then concentrated in vacuo. The resultant residue was 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 product was triturated with MeOH/diethylether to yield the title compound as a light brown solid (20 mg, 39%). 1H NMR (d6-DMSO, 400 MHz) 11.32 (1H, s), 8.69 (1H, s), 7.98 (1H, s), 7.49 (1H, dd, J=11.0, 2.0 Hz), 7.40 (2H, s), 7.18-7.14 (1H, m), 6.74 (1H, s), 5.92 (1H, t, J=8.8 Hz), 4.65 (1H, t, J=5.6 Hz), 3.75 (2H, t, J=5.0 Hz), 3.46 (2H, q, J=5.0 Hz). LCMS (Method A): RT=8.14 min, M+H+=457.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe resultant residue was dissolved in ethyl acetate (10 mL)
  3. washwashed with aqueous saturated sodium bicarbonate solution (10 mL)
  4. extractionthe aqueous fraction extracted twice with ethyl acetate (2×10 mL)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe product was triturated with MeOH/diethylether

Sources & evidence

ORD record
ord-e7ab0fd328324619a7ee52d2cfcef0ac
Source dataset
uspto-grants-2013_07
Patent number
US08486963B2

Reaction notes

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