Trifluoroacetic acid → HCID 73504793, compound

HRID 590806Notes

Reaction equation

HRID 590806 reaction equation
[C:1]1([C@H:7]([NH:9][C:10](=[O:44])[NH:11][C:12]2[N:17]=[CH:16][C:15]3[C:18]([NH:40][C:41](=[O:43])[CH3:42])=[N:19][N:20](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:14]=3[CH:13]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([C@H:7]([NH:9][C:10](=[O:44])[NH:11][C:12]2[N:17]=[CH:16][C:15]3[C:18]([NH:40][C:41](=[O:43])[CH3:42])=[N:19][NH:20][C:14]=3[CH:13]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 118272018HCID 118272018, compound

Product 1

HCID 73504793HCID 73504793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)—N-(6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide (900 mg, 1.550 mmol) and triethylsilane (0.495 mL, 3.10 mmol) in DCM (14 mL) was treated with TFA (7.16 mL, 93 mmol). The reaction was stirred at room temperature for 1 h. The reaction mixture was evaporated in vacuo and the residue was partitioned between EtOAc and sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organics were washed with sat. aq. NaHCO3, brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by flash chromatography (0-10% MeOH/DCM) to afford (R)—N-(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide. MS ESI calc'd. For C17H18N6O2 [M+1]+ 339. found 339. 1H NMR (500 MHz, DMSO-d6) δ 12.56 (s, 1H), 10.71 (s, 1H), 8.99 (s, 1H), 8.94 (s, 1H), 7.80-7.72 (br s, 1H), 7.50 (s, 1H), 7.36-7.29 (m, 4H), 7.26-7.19 (m, 1H), 4.91-4.81 (m, 1H), 2.09 (s, 3H), 1.39 (d, J=6.9, 3H).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc and sat. aq. NaHCO3
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organics were washed with sat. aq. NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-e77f444b2d2e4b41995f5fb92e3e9e93
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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