N-tert-butyl-5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide → 5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide

HRID 1484961Notes

Reaction equation

HRID 1484961 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([C@@H:26]4[CH2:28][C@H:27]4[CH3:29])[NH:23][N:22]=3)[C:17]([Cl:30])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[Cl:30][C:17]1[C:18]([NH:20][C:21]2[CH:25]=[C:24]([C@@H:26]3[CH2:28][C@H:27]3[CH3:29])[NH:23][N:22]=2)=[N:19][C:14]([C:11]2[S:10][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:13][CH:12]=2)=[N:15][CH:16]=1

Participants

3

Reactant 1

HCID 66927457N-tert-butyl-5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide

Product 1

HCID 669275575-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamideYield 89.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of N-tert-butyl-5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (90 mg, 0.19 mmol) in TFA (5 mL) was heated to reflux for 0.5 h. After concentration, the resulting residue was dilute with EtOAc and washed with water, saturate NaHCO3, brine, dried (Na2SO4) and filtered. The filtrate was concentrated to afford the title compound 5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 320) (70 mg, 89%). LC-MS (m/z)=411 [M+H]% 1H NMR (400 MHz, DMSO-d6) δ 0.78-0.81 (m, 1H), 0.92-0.95 (m, 1H), 1.16 (m, 4H), 1.64-1.65 (m, 1H), 6.37 (s, 1H), 7.58 (d, J=4.0 Hz, 1H), 7.75 (d, J=3.6 Hz, 1H), 7.81 (s, 2H), 8.45 (s, 1H), 9.42 (s, 1H), 12.26 (s, 1H).

Workup

  1. temperatureto reflux for 0.5 h
  2. concentrationAfter concentration
  3. additionthe resulting residue was dilute with EtOAc
  4. washwashed with water
  5. concentrationsaturate NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-99bc9668174c40dc89988e55b877ec68
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

Loading…