HCID 58169506, compound → HCID 58169442, compound

HRID 1484979Notes

Reaction equation

HRID 1484979 reaction equation
[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:30]=[C:29]([CH:31]3[CH2:33][CH2:32]3)[NH:28][N:27]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([S:13]([NH:16][NH:17]C(OC(C)(C)C)=O)(=[O:15])=[O:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:30]=[C:29]([CH:31]3[CH2:33][CH2:32]3)[NH:28][N:27]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([S:13]([NH:16][NH2:17])(=[O:14])=[O:15])=[CH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 58169506HCID 58169506, compound

Product 1

HCID 58169442HCID 58169442, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl 2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophen-2-ylsulfonyl)hydrazinecarboxylate (23 mg, 0.05 mmol, 1.0 equiv.) was stirred in TFA at r.t. for 30 min. The reaction was concentrated and to the residue was added aqueous NaHCO3 and extracted with EA (3×). The combined EA layers were dried (Na2SO4), filtered, concentrated and washed with ether to afford the 5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonohydrazide (Compound 251) (8 mg, 44%). LC-MS (m/z)=412 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 0.75-0.76 (m, 2H), 0.98-0.99 (m, 2H), 1.91-1.95 (m, 1H), 4.23 (d, J=7.2 Hz, 2H), 6.41 (s, 1H), 7.94 (s, 1H), 8.30 (d, J=1.2 Hz, 1H), 8.46 (s, 2H), 9.47 (d, J=7.6 Hz, 1H), 12.37 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated and to the residue
  2. additionwas added aqueous NaHCO3
  3. extractionextracted with EA (3×)
  4. dry with materialThe combined EA layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washwashed with ether

Sources & evidence

ORD record
ord-852c220b508b41a2a052873b53a17621
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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