Trifluoroacetic acid → HCID 178467666, compound

HRID 571427Notes

Reaction equation

HRID 571427 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[C:9]2[CH:10]=[N:11][C:12]([NH:14][C:15]([NH:17][C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])=[O:16])=[CH:13][C:8]=2[N:7](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:6]=1)[CH3:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[CH2:1]([O:3][CH2:4][C:5]1[C:9]2[CH:10]=[N:11][C:12]([NH:14][C:15]([NH:17][C@@H:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH3:19])=[O:16])=[CH:13][C:8]=2[NH:7][N:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 117601729HCID 117601729, compound

Product 1

HCID 178467666HCID 178467666, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of (R)-1-(3-(ethoxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (130 mg, 0.223 mmol) and trifluoroacetic acid (0.856 ml, 11.17 mmol) in dichloromethane (2.0 ml) was added triethylsilane (39.0 mg, 0.335 mmol). The resulting mixture was allowed to stir at rt for 18 h. The reaction was concentrated in vacuo and submitted for reversed phase HPLC purification to provide the desired product (28.5 mg, 0.063 mmol, 28.1% yield). MS ESI calc'd. for C18H21N5O2 [M+H]+ 340, found 340.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customphase HPLC purification

Sources & evidence

ORD record
ord-aa5e953e273c4ef891dcf0804b05341e
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

Loading…