Hydrochloric Acid → 8-(4-Cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid (2-hydroxy-ethoxy)-amide

HRID 2067034Notes

Reaction equation

HRID 2067034 reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]2[CH:16]=[N:17][CH:18]=[C:12]2[C:11]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:29][CH2:28][CH2:27]2)=[CH:22][C:21]=1[F:30])=[O:9])=C.Cl>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]2[CH:16]=[N:17][CH:18]=[C:12]2[C:11]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:29][CH2:28][CH2:27]2)=[CH:22][C:21]=1[F:30])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 595651898-(4-Cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid (2-vinyloxy-ethoxy)-amide

Product 1

HCID 441373658-(4-Cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid (2-hydroxy-ethoxy)-amideYield 11.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-(4-Cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid (2-vinyloxy-ethoxy)-amide (149 mg, 0.36 mmol) was dissolved in methanol (2 mL) and treated with 1M HCl (1.5 mL). The reaction mixture was stirred at room temperature for 2 hours. The solvents were removed in vacuo and the residue was purified by preparative HPLC (Gemini 5 micron C18 250×21.20 mm column, 0.1% formic acid, gradient acetonitrile/water, 5 to 98%, ramp time 20 minutes) to afford the title compound as a yellow solid (16 mg, 11%). LCMS (method A): RT=7.40 min, [M+H]+=385. 1H NMR (DMSO-d6):11.59 (1H, s), 10.60 (1H, s), 8.32 (1H, s), 7.82 (1H, d, J=7.7 Hz), 7.24 (1H, d, J=8.5 Hz), 7.15 (1H, d, J=11.2 Hz), 7.07 (1H, d, J=8.11 Hz), 6.79 (1H, d, J=7.3 Hz), 6.33 (1H, s), 4.73 (1H, s), 3.69 (2H, t, J=4.8 Hz), 3.61 (2H, t, J=5.0 Hz), 3.57 (1H, d, J=8.8 Hz), 2.36 (2H, m), 2.12 (2H, m), 1.96 (1H, m), 1.83 (1H, m).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by preparative HPLC (Gemini 5 micron C18 250×21.20 mm column, 0.1% formic acid, gradient acetonitrile/water, 5 to 98%, ramp time 20 minutes)

Sources & evidence

ORD record
ord-8c6990892abe4e39b53c5d7ddc4203aa
Source dataset
uspto-grants-2012_10
Patent number
US08293763B2

Reaction notes

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