Sulfanilamide → HCID 25185035, compound

HRID 1770860Notes

Reaction equation

HRID 1770860 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][F:18])=[CH:11][CH:10]=2)[C:5]([F:19])=[CH:4][N:3]=1.[S:20]([NH2:30])(=[O:29])([C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)=[O:21]>C(O)(C)C.C(O)(C(F)(F)F)=O>[NH2:30][S:20]([C:22]1[CH:23]=[CH:24][C:25]([NH:28][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][F:18])=[CH:11][CH:10]=3)[C:5]([F:19])=[CH:4][N:3]=2)=[CH:26][CH:27]=1)(=[O:21])=[O:29]

Participants

5

Reactant 2

HCID 5333SulfanilamideHCID 57562949HCID 57562949, compound

Product 1

HCID 25185035HCID 25185035, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-5-fluoro-N4-[4-(3-fluoropropyl)phenyl]-4-pyrimidineamine (100 mg) and sulfanilamide (100 mg) were suspended in isopropanol (1 mL) and TFA (5 drops). The solution was heated at 100° C. overnight. The solution was evaporated and purified by flash column chromatography (2.0 M NH3/MeOH in dichloromethane=1-3%) and recrystallized from ethyl acetate to give N2-(4-aminosulfonylphenyl)-5-fluoro-N4-[4-(3-fluoropropyl)phenyl]-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 1.89-2.02 (m, 2H), 2.67 (t, J=8.1 Hz, 2H), 4.38 (t, J=5.7 Hz, 1H), 4.53 (t, J=5.7 Hz, 1H), 7.11 (br, 2H), 7.19 (d, J=8.1 Hz, 2H), 7.60 (d, J=8.7 Hz, 2H), 7.65 (d, J=8.1 Hz, 2H), 7.80 (d, J=8.7 Hz, 2H), 8.12 (d, J=3.9 Hz, 1H), 9.38 (br, 1H), 9.57 (br, 1H); 19F NMR (282 MHz, DMSO-d6): δ −201.79; LCMS: purity: 91.96%; MS (m/e): 420.74 (MH+).

Workup

  1. customThe solution was evaporated
  2. custompurified by flash column chromatography (2.0 M NH3/MeOH in dichloromethane=1-3%)
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-75d9e9b1c1e245a09250d06a958debc0
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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