Hydrochloric Acid → HCID 69671569, compound

HRID 626791Notes

Reaction equation

HRID 626791 reaction equation
[F:1][C:2]1[C:3]([N:10]2[CH:27]=[C:13]3[C:14]([NH:19][C:20]4[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22][N:21]=4)=[N:15][CH:16]=[C:17]([F:18])[C:12]3=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[ClH:28]>CC(O)C>[ClH:28].[F:1][C:2]1[C:3]([N:10]2[CH:27]=[C:13]3[C:14]([NH:19][C:20]4[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22][N:21]=4)=[N:15][CH:16]=[C:17]([F:18])[C:12]3=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69671102HCID 69671102, compound

Product 1

HCID 69671569HCID 69671569, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 3-fluoro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]-benzonitrile (46 mg, 0.13 mmol) in 1.25 N HCl in propan-2-ol solution (2.5 mL) was heated at 50° C. for 2 hours. The resultant mixture was concentrated under reduced pressure and the residue was dried at 50° C. under high vacuum overnight to afford the title compound as an off-white solid (60 mg, 100% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.64 (br s, 1H), 9.06 (s, 1H), 8.39 (br s, 1H), 8.15 (d, J=3.5 Hz, 1H), 8.11-8.02 (m, 2H), 7.97-7.90 (m, 1H), 2.61 (s, 3H). LCMS (Method B): RT=2.92 min, m/z: 364 [M+H+].

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. customthe residue was dried at 50° C. under high vacuum overnight

Sources & evidence

ORD record
ord-0e2acce53fca44b69f963e623c961aaf
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

Loading…