HCID 90242256, compound → HCID 76900610, compound

HRID 880281Notes

Reaction equation

HRID 880281 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH:12]([OH:37])[CH2:13][NH:14][C:15]([C:17]1[CH:18]=[C:19]([CH:34]=[CH:35][CH:36]=1)[CH2:20][N:21]1[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]1)=[O:16]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH:12]([OH:37])[CH2:13][NH:14][C:15](=[O:16])[C:17]1[CH:36]=[CH:35][CH:34]=[C:19]([CH2:20][N:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[CH:18]=1

Participants

4

Reactant 1

HCID 90242256HCID 90242256, compound

Product 1

HCID 76900610HCID 76900610, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of tert-butyl 4-(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)carbamoyl)benzyl)piperazine-1-carboxylate (160 mg, 0.314 mmol) in DCM (2 mL) and TFA (2 mL) was stirred at 27° C. for 16 h. The solution was concentrated and the residue was purified by prep-HPLC to give the title product (89 mg, Yield 69.0%). 1H NMR (D2O, 400 MHz): δ 7.66-7.56 (m, 2H), 7.51-7.44 (m, 1H), 7.44-7.37 (m, 1H), 7.16-7.06 (m, 3H), 7.02 (d, J=7.3 Hz, 1H), 4.11 (quin, J=5.9 Hz, 1H), 3.73-3.60 (m, 2H), 3.56-3.49 (m, 2H), 3.49-3.42 (m, 1H), 3.41-3.32 (m, 1H), 2.86-2.75 (m, 8H), 2.68-2.58 (m, 2H), 2.56-2.32 (m, 4H). LCMS (m/z): 409.2 (M+1).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-b4ef1e2230fa490b897ff223a5325f73
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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