3-(2-Fluoro-4-iodo-phenylamino)-thieno[2,3-c]pyridine-2-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide → 3-(2-Fluoro-4-iodo-phenylamino)-thieno[2,3-c]pyridine-2-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amide

HRID 1366785Notes

Reaction equation

HRID 1366785 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][O:8][NH:9][C:10]([C:12]2[S:20][C:15]3=[CH:16][N:17]=[CH:18][CH:19]=[C:14]3[C:13]=2[NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])=[O:11])[CH2:4][O:3]1>CO.Cl>[OH:6][C@H:5]([CH2:4][OH:3])[CH2:7][O:8][NH:9][C:10]([C:12]1[S:20][C:15]2=[CH:16][N:17]=[CH:18][CH:19]=[C:14]2[C:13]=1[NH:21][C:22]1[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=1[F:29])=[O:11]

Participants

4

Reactant 1

HCID 597038943-(2-Fluoro-4-iodo-phenylamino)-thieno[2,3-c]pyridine-2-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide

Product 1

HCID 250297773-(2-Fluoro-4-iodo-phenylamino)-thieno[2,3-c]pyridine-2-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amideYield 59.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

3-(2-Fluoro-4-iodo-phenylamino)-thieno[2,3-c]pyridine-2-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide (40 mg, 0.07 mmol) was dissolved in methanol (1 ml) and concentrated hydrochloric acid (1 drop) added. The mixture was allowed to stir for 2 hours then evaporated to dryness to give a residue. The residue was partitioned between aqueous saturated NaHCO3 solution (3 ml), water (20 ml) and DCM (20 ml). The organic layer was separated, dried over sodium sulphate, filtered and evaporated to give a yellow solid. The solid was purified by flash chromatography (Si-SPE, DCM:MeOH, gradient 99:1 to 92:8) to afford the title compound as a yellow solid (21 mg, 57%). LCMS (method A): RT=7.12 min, M+H+=504. 1H NMR (d4-MeOH, 400 MHz) 9.15 (s, 1H), 8.38 (d, J=5.7 Hz, 1H), 7.52 (dd, J=10.6 Hz, 2.0 Hz, 1H), 7.44 (dd, J=5.7 Hz, 1.0 Hz, 1H), 7.32 (ddd, J=8.5 Hz, 2.0 Hz, 1.0 Hz, 1H), 6.56 (dd, J=8.5 Hz, 8.5 Hz, 1H), 4.00-4.13 (m, 1H), 3.85-3.95 (m, 2H), 3.54-3.65 (m, 2H).

Workup

  1. customthen evaporated to dryness
  2. customto give a residue
  3. customThe residue was partitioned between aqueous saturated NaHCO3 solution (3 ml), water (20 ml) and DCM (20 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a yellow solid
  9. customThe solid was purified by flash chromatography (Si-SPE, DCM:MeOH, gradient 99:1 to 92:8)

Sources & evidence

ORD record
ord-48ad3abe9bbe40fe86e20a59237a026b
Source dataset
uspto-grants-2011_02
Patent number
US07893085B2

Reaction notes

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