HCID 178449968, compound → HCID 178514697, compound

HRID 1484989Notes

Reaction equation

HRID 1484989 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)[C:17]([Cl:23])=[C:16]([NH:24][C:25]3[NH:29][N:28]=[C:27]([CH:30]4[CH2:32][CH2:31]4)[CH:26]=3)[N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[Cl:23][C:17]1[C:18]([CH:20]2[CH2:22][CH2:21]2)=[N:19][C:14]([C:11]2[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=2)=[N:15][C:16]=1[NH:24][C:25]1[NH:29][N:28]=[C:27]([CH:30]2[CH2:32][CH2:31]2)[CH:26]=1

Participants

3

Reactant 1

HCID 178449968HCID 178449968, compound

Product 1

HCID 178514697HCID 178514697, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of N-tert-butyl-5-(5-chloro-4-cyclopropyl-6-(3-cyclopropyl-1H-pyrazol-5-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (60 mg, 0.12 mmol) in trifluoroacetic acid (5 mL) was stirred at 60° C. After 0.5 h, the solution was evaporated to give the crude product, which was recrystallized from ether to afford 5-(5-chloro-4-cyclopropyl-6-(3-cyclopropyl-1H-pyrazol-5-ylamino)pyrimidin-2-yl)thiophene-2 sulfonamide (Compound 304) (25 mg, 48%). LC-MS (m/z)=436.9 [M+H]+; δ (400 MHz, DMSO-d6); 0.73-0.77 (m, 2H), 0.96-0.99 (m, 2H), 1.12-1.14 (m, 4H), 1.91 (m, 1H), 2.43-2.47 (m, 1H), 6.39 (s, 1H), 7.48 (s, 2H), 7.96 (d, J=1.6 Hz, 1H), 8.18 (d, J=1.2 Hz, 1H), 9.18 (s, 1H)

Workup

  1. customthe solution was evaporated
  2. customto give the crude product, which
  3. customwas recrystallized from ether

Sources & evidence

ORD record
ord-cdd4d8a1b1f94b79868bd51d7cafc320
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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