Hydrochloric Acid → HCID 71511348, compound

HRID 2171883Notes

Reaction equation

HRID 2171883 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([F:40])[C:6]([NH:29][C@@H:30]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:31][S:32]([OH:35])(=[O:34])=[O:33])=[N:7][C:8]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([F:18])[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1)#[N:2].Cl>CC#N>[C:1]([C:3]1[CH:4]=[C:5]([F:40])[C:6]([NH:29][C@@H:30]([C:36]([CH3:38])([CH3:37])[CH3:39])[CH2:31][S:32]([OH:35])(=[O:33])=[O:34])=[N:7][C:8]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([F:18])[CH:16]=2)[NH:11][CH:10]=1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86714762HCID 86714762, compound

Product 1

HCID 71511348HCID 71511348, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-2-((5-cyano-3-fluoro-6-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl)amino)-3,3-dimethylbutane-1-sulfonic acid, 101a, (0.12 g, 0.21 mmol) in CH3CN (5 mL) was added HCl (2 mL of 4M solution in dioxane). The reaction mixture was heated at 100° C. for 18 hours in a pressure vial and then cooled to room temperature. The solvent was removed under reduced pressure and the product was purified by preparative HPLC chromatography (10-80% CH3CN/water, 0.5% TFA, 15 min) to give 42 mg of the desired product as an off-white solid: 1H NMR (400 MHz, MeOD) δ 8.44 (s, 1H), 8.34 (dd, J=9.2, 2.6 Hz, 1H), 8.22 (d, J=5.7 Hz, 1H), 8.13 (s, 1H), 5.16 (m, 1H), 3.46-3.33 (m, 3H), 1.10 (s, 9H); LC/MS (10-90% ACN/water 5 min with 0.9% TFA, C18) m/z 449.22 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe product was purified by preparative HPLC chromatography (10-80% CH3CN/water, 0.5% TFA, 15 min)

Sources & evidence

ORD record
ord-0e4a4ad252b94fa497e857a7189a06ae
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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