Trifluoroacetic acid → HCID 44196949, compound

HRID 340136Notes

Reaction equation

HRID 340136 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:44]=[CH:43][C:12]([CH2:13][N:14]([CH2:33][CH2:34][NH:35]C(=O)OC(C)(C)C)[C:15](=[O:32])[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]4[C@H:30]([CH3:31])[CH2:29][CH2:28][C:24]=4[N:25]=[CH:26][N:27]=3)=[CH:18][CH:17]=2)=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:35][CH2:34][CH2:33][N:14]([CH2:13][C:12]1[CH:11]=[CH:10][C:9]([Cl:8])=[CH:44][CH:43]=1)[C:15](=[O:32])[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]3[C@H:30]([CH3:31])[CH2:29][CH2:28][C:24]=3[N:25]=[CH:26][N:27]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67437078HCID 67437078, compound

Product 1

HCID 44196949HCID 44196949, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (182 μL, 2.36 mmol) was added to a solution of (R)-tert-butyl 2-(N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzamido)ethylcarbamate (49 mg, 0.094 mmol) in DCM (1 mL). The mixture was stirred at room temperature for 1.5 hours. The mixture was concentrated in vacuo. The crude product was purified by reverse phase HPLC to give (R)-N-(2-aminoethyl)-N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzamide as an oil (9 mg, 22%). MS (APCI+) [M+H]+421.2. 1H NMR (D2O, 500 MHz) δ 9.09 (s, 1H), 7.81 (d, J=8.5 Hz, 2H), 7.63 (d, J=8.0 Hz, 2H), 7.35 (d, J=8.5 Hz, 2H), 7.15 (D, J=8.0 Hz, 2H), 4.63 (s, 2H), 3.87 (t, J=6.5 Hz, 2H), 3.82-3.79 (m, 1H), 3.26-3.11 (m, 4H), 2.63 (s, 2H), 2.50-2.42 (m, 1H), 1.86-1.81 (m, 1H), 0.86 (s, J=7.00 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-26120e4e4cc24674a92431572470c029
Source dataset
uspto-grants-2014_11
Patent number
US08895566B2

Reaction notes

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