Hydrochloric Acid → HCID 67112152, compound

HRID 594970Notes

Reaction equation

HRID 594970 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[N:9]=[CH:10][C:5]2=[CH:4][N:3]=1.[CH3:23][N:24]1[CH:28]=[C:27]([NH2:29])[CH:26]=[N:25]1.Cl>C(O)(C)C>[CH3:23][N:24]1[CH:28]=[C:27]([NH:29][C:2]2[N:7]=[C:6]3[N:8]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[N:9]=[CH:10][C:5]3=[CH:4][N:3]=2)[CH:26]=[N:25]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 47709901-methyl-1H-pyrazol-4-amineHCID 86671733HCID 86671733, compound

Product 1

HCID 67112152HCID 67112152, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of N-(2-((6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)methanesulfonamide (53 mg, 0.16 mmol), 1-methyl-1H-pyrazol-4-amine (0.24 mmol) and HCl (0.26 mmol, 4M in dioxane) in isopropanol was heated in the microwave at 140° C. for 1 h. After cooling to rt the mixture was washed with H2O, extracted with DCM then dried using a hydrophobic frit. The organic phase was concentrated in vacuo. Purification was performed by prep. HPLC. The desired fractions were concentrated in vacuo to afford the title compound. 1H NMR (d6-DMSO) δ 9.88 (s, 1H), 9.44 (s, 1H), 8.94 (s, 1H), 8.11 (s, 1H), 7.99 (s, 1H), 7.48 (s, 1H), 7.38 (d, 1H), 7.30 (t, 1H), 7.13 (t, 1H), 6.71 (s, 1H), 5.71 (s, 2H), 3.79 (s, 3H), 3.06 (s, 3H); LC-MS method B, (ES+) 399, RT=7.14 min

Workup

  1. temperatureAfter cooling to rt the mixture
  2. washwas washed with H2O
  3. extractionextracted with DCM
  4. customthen dried
  5. concentrationThe organic phase was concentrated in vacuo
  6. customPurification
  7. concentrationThe desired fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-67f9455a1845449d886d326feb1436df
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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