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

HRID 1366778Notes

Reaction equation

HRID 1366778 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][O:8][NH:9][C:10]([C:12]2[S:20][C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[C:13]=2[NH:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=2[F:29])=[O:11])[CH2:4][O:3]1>CO>[OH:6][C@H:5]([CH2:4][OH:3])[CH2:7][O:8][NH:9][C:10]([C:12]1[S:20][C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[C:13]=1[NH:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=1[F:29])=[O:11]

Participants

3

Reactant 1

HCID 597038953-(4-Bromo-2-fluoro-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide

Product 1

HCID 250297763-(4-Bromo-2-fluoro-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(4-bromo-2-fluoro-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide (18 mg, 0.036 mmol) in methanol (1 ml) was loaded onto an Isolute® SCX-2 cartridge (5 g). The cartridge was then washed with methanol (15 ml) before the desired product was eluted using 2M ammonia in MeOH and the eluent collected then concentrated to give a residue. The residue was purified by flash chromatography (Si-SPE, DCM:MeOH, gradient 100:0 to 94:6) to afford the title compound as an off white solid (9 mg, 53%): LCMS (method A): RT=5.59 min, M+H+=456/458. 1H NMR (d4-MeOH, 400 MHz) 8.60 (s, 1H), 8.40 (d, J=5.7 Hz, 1H), 7.94 (d, J=5.7 Hz, 1H), 7.39 (dd, J=10.6 Hz, 2.2 Hz, 1H), 7.16 (d, J=8.5 Hz, 1H), 6.80 (dd, J=8.5 Hz, 8.5 Hz, 1H), 4.01-4.10 (m, 1H), 3.89-4.00 (m, 2H), 3.57-3.67 (m, 2H).

Workup

  1. washThe cartridge was then washed with methanol (15 ml) before the desired product
  2. washwas eluted
  3. customthe eluent collected
  4. concentrationthen concentrated
  5. customto give a residue
  6. customThe residue was purified by flash chromatography (Si-SPE, DCM:MeOH, gradient 100:0 to 94:6)

Sources & evidence

ORD record
ord-3be616ae65e34656aa37cae937051906
Source dataset
uspto-grants-2011_02
Patent number
US07893085B2

Reaction notes

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