Trifluoroacetic acid → HCID 178426360, compound

HRID 474379Notes

Reaction equation

HRID 474379 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C@H:15]1[CH2:20][CH2:19][C@@H:18]([CH2:21][N:22]2[C:26]3=[N:27][C:28]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([S:39](=[O:42])(=[O:41])[NH2:40])[CH:33]=4)=[N:29][CH:30]=[C:25]3[CH:24]=[N:23]2)[CH2:17][CH2:16]1)(C)(C)C>C(Cl)Cl>[NH2:14][C@@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:21][N:22]2[C:26]3=[N:27][C:28]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([S:39]([NH2:40])(=[O:42])=[O:41])[CH:33]=4)=[N:29][CH:30]=[C:25]3[CH:24]=[N:23]2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178426361HCID 178426361, compound

Product 1

HCID 178426360HCID 178426360, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.0 mL, 13 mmol) was added drop-wise over about 1 min to a 100 mL round-bottomed flask containing a solution of tert-butyl-cis-4-((6-(4-methyl-3-sulfamoylphenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate (0.55 g, 1.1 mmol, Example #B.1.1) in DCM (5 mL) at ambient temperature. The reaction mixture was allowed to stir for about 2 h then concentrated under reduced pressure. The crude product was purified by RP-HPLC (Table 2, Method b) to give 5-(1-((cis-4-aminocyclohexyl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methylbenzenesulfonamide (0.435 g. 95%) as a white solid. LC/MS (Table 2, Method a) Rt=1.39 min; MS m/z: 414 (M+H)+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe crude product was purified by RP-HPLC (Table 2, Method b)

Sources & evidence

ORD record
ord-2542f1cfe1dd43fca5acf4179f5beb09
Source dataset
uspto-grants-2014_01
Patent number
US08637529B2

Reaction notes

Loading…