HCID 178449967, compound → HCID 178514696, compound

HRID 1484986Notes

Reaction equation

HRID 1484986 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([CH:20]3[CH2:22][CH2:21]3)[CH:17]=[C:16]([NH:23][C:24]3[NH:28][N:27]=[C:26]([CH:29]4[CH2:31][CH2:30]4)[CH:25]=3)[N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[CH:20]1([C:18]2[CH:17]=[C:16]([NH:23][C:24]3[NH:28][N:27]=[C:26]([CH:29]4[CH2:31][CH2:30]4)[CH:25]=3)[N:15]=[C:14]([C:11]3[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=3)[N:19]=2)[CH2:21][CH2:22]1

Participants

3

Reactant 1

HCID 178449967HCID 178449967, compound

Product 1

HCID 178514696HCID 178514696, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of N-tert-butyl-5-(4-cyclopropyl-6-(3-cyclopropyl-1H-pyrazol-5-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (50 mg, 0.1 mmol) in trifluoroacetic acid (5 mL) was stirred at 60° C. After 0.5 h, the solution was evaporated to give a residue which was recrystallized from ether to afford 5-(4-cyclopropyl-6-(3-cyclopropyl-1H-pyrazol-5-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (VRCompound 298) (21 mg, 52%). LC-MS (m/z)=403.1 [M+H]+; δ (400 MHz, DMSO-d6); 0.71-0.74 (m, 2H), 0.93-1.02 (m, 6H), 1.88-2.00 (m, 2H), 6.19 (bs, 1H), 6.93 (bs, 1H), 7.46 (s, 2H), 8.01 (s, 1H), 8.14 (b, 1H), 9.86 (s, 1H).

Workup

  1. customthe solution was evaporated
  2. customto give a residue which
  3. customwas recrystallized from ether

Sources & evidence

ORD record
ord-72344fb0356d4244afd4f561ea8d04a9
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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