Hydrochloric Acid → 4-(2-Fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amide

HRID 79059Notes

Reaction equation

HRID 79059 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][O:8][NH:9][C:10]([C:12]2[C:13]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=3[F:29])=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][N:16]=[CH:15]3)=[O:11])[CH2:4][O:3]1.Cl.O1CCOCC1>CO>[OH:6][C@H:5]([CH2:4][OH:3])[CH2:7][O:8][NH:9][C:10]([C:12]1[C:13]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][N:16]=[CH:15]2)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 866562454-(2-Fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid ((R)-2,2-dimethyl-[1,3]-dioxolan-4-ylmethoxy)amide

Product 1

HCID 446031434-(2-Fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide (135 mg, 0.26 mmol) in methanol (4 mL) was added hydrochloric acid in dioxane (2 mL, 4N, 8 mmol). The reaction mixture was stirred at room temperature for 1 hour before being concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—SPE, gradient 0-10% methanol in DCM) to yield the title compound as an off white solid (94 mg, 75%). LCMS (Method A): RT=7.67 min, [M+H]+=487. 1H NMR (DMSO-d6, 400 MHz) 13.20 (1H, s), 11.67 (1H, s), 9.94 (1H, s), 7.66 (1H, dd, J=10.30, 1.92 Hz), 7.47 (1H, d, J=8.79 Hz), 7.45-7.41 (1H, m), 7.22 (1H, s), 7.01 (1H, d, J=8.78 Hz), 6.92 (1H, t, J=8.64 Hz), 3.92-3.85 (1H, m), 3.76-3.58 (2H, m), 3.41-3.31 (2H, m).

Workup

  1. concentrationbefore being concentrated in vacuo

Sources & evidence

ORD record
ord-b4d8a4eb4637456abe787d2e2cde9742
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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