Trifluoroacetic acid → HCID 89810787, compound

HRID 1485574Notes

Reaction equation

HRID 1485574 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:18][CH:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)[C:16]=3[N:17]=2)=[CH:4][C:3]=1[NH:32][S:33]([C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1[F:43])(=[O:35])=[O:34].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([NH:32][S:33]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=2[F:43])(=[O:34])=[O:35])=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:18][CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[C:16]=3[N:17]=2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66558476HCID 66558476, compound

Product 1

HCID 89810787HCID 89810787, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(6-(6-chloro-5-(2,4-difluorophenylsulfonamido)pyridin-3-yl)pyrido[3,2-d]pyrimidin-4-ylamino)piperidine-1-carboxylate (1.28 g, 2.03 mmol) in DCM (20 mL) was added TFA (3.10 mL, 40.5 mmol) at 0° C. The reaction mixture was stirred for 4 h at room temperature and removed the solvent in vacuo. DCM was poured into the residue, and neutralized with aq. Na2HCO3. The resulting solid was filtered and washed with MeOH and EtOAc to give N-(2-chloro-5-(4-(piperidin-4-ylamino)pyrido[3,2-d]pyrimidin-6-yl)pyridine-3-yl)-2,4-difluorobenzenesulfonamide (954 mg, 89%) as a pale yellow solid. 1H-NMR (DMSO-d6, Varian 400 MHz) δ 1.84-2.00 (2H, m), 2.12-2.24 (2H, m), 3.04-3.18 (2H, m), 3.32-3.46 (2H, m), 4.38-4.52 (1H, m), 7.07 (1H, dt, J=2.0, 8.4 Hz), 7.22 (1H, dt, J=2.4, 10.0 Hz), 7.83-7.92 (1H, m), 8.04 (1H, d, J=8.0 Hz), 8.11 (1H, d, J=8.8 Hz), 8.19 (1H, d, J=8.8 Hz), 8.26 (1H, d, J=2.4 Hz), 8.43 (2H, brs), 8.52 (1H, s), 8.59 (1H, d, J=2.4 Hz). m/z=532.2 [M+1]+.

Workup

  1. customremoved the solvent in vacuo
  2. additionDCM was poured into the residue
  3. filtrationThe resulting solid was filtered
  4. washwashed with MeOH and EtOAc

Sources & evidence

ORD record
ord-1a3713787e3e452eb5654d92b6eb785a
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Reaction notes

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