Trifluoroacetic acid → HCID 178432472, compound

HRID 1811895Notes

Reaction equation

HRID 1811895 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2C2CCCCO2)=[C:4]([C:17]2[C:18]([NH:34][C:35]3[C:36]4[CH:37]=[N:38][N:39](C5CCCCO5)[C:40]=4[CH:41]=[CH:42][CH:43]=3)=[N:19][CH:20]=[C:21]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=3)[CH:22]=2)[N:3]=1.[C:50]([OH:56])([C:52]([F:55])([F:54])[F:53])=[O:51]>C(Cl)Cl>[F:53][C:52]([F:55])([F:54])[C:50]([OH:56])=[O:51].[CH3:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([C:17]2[C:18]([NH:34][C:35]3[C:36]4[CH:37]=[N:38][NH:39][C:40]=4[CH:41]=[CH:42][CH:43]=3)=[N:19][CH:20]=[C:21]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=3)[CH:22]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66611958N-(3-(2-Methyl-9-(tetrahydro-2H-pyran-2-YL)-9H-purin-6-YL)-5-(4-(methylsulfonyl)benzyl)pyridin-2-YL)-1-(tetrahydro-2H-pyran-2-YL)-1H-indazol-4-amine

Product 1

HCID 178432472HCID 178432472, compoundYield 8.22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)-5-(4-(methylsulfonyl)benzyl)pyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-amine (111 mg, 0.164 mmol) in DCM (3.0 mL) was treated with TFA (1.0 mL) and allowed to stand for 2 h. The mixture was concentrated, azeotroped with toluene, purified by prep HPLC, and the pure fractions were concentrated and triturated with MeOH to give pure N-(3-(2-methyl-9H-purin-6-yl)-5-(4-(methylsulfonyl)benzyl)pyridin-2-yl)-1H-indazol-4-amine trifluoroacetate (8.4 mg, 0.013 mmol, 8.22% yield) as an orange crystalline solid. 1H NMR (400 MHz, d6-DMSO) δ 13.12 (br. s., 1H); 12.61 (br. s., 1H); 9.68 (br. s., 1H); 8.63 (s, 1H); 8.36 (d, J=2.15 Hz, 1H); 8.26 (s, 1H); 8.08 (d, J=7.63 Hz, 1H); 7.87 (d, J=8.22 Hz, 2H); 7.59 (d, J=8.22 Hz, 2H); 7.31 (t, J=8.02 Hz, 1H); 7.16 (d, J=8.41 Hz, 1H); 4.17 (s, 2H); 3.16 (s, 3H); 2.93 (s, 3H). m/z (ESI, +ve ion) 511.0 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customazeotroped with toluene
  3. custompurified by prep HPLC
  4. concentrationthe pure fractions were concentrated
  5. customtriturated with MeOH

Sources & evidence

ORD record
ord-2c303b82b78e4c97a1075413f0a3b691
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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