HCID 58299986, compound → 9-Cyclopentyl-N-(5-Piperazin-1-Ylpyridin-2-Yl)pyrido[4,5]pyrrolo[1,2-D]pyrimidin-2-Amine

HRID 79107Notes

Reaction equation

HRID 79107 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)=[CH:18][CH:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][N:37]=[CH:38][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:20][N:21]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][N:37]=[CH:38][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 1

HCID 58299986HCID 58299986, compound

Product 1

HCID 441325859-Cyclopentyl-N-(5-Piperazin-1-Ylpyridin-2-Yl)pyrido[4,5]pyrrolo[1,2-D]pyrimidin-2-AmineYield 98.5%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of compound 6 (3.28 g, 6.37 mmol) in TFA/DCM (60, 1:1) was stirred at room temperature for 30 min. The reaction mixture was concentrated and the residue was purified by chromatography on silica gel eluting with CH2Cl2/methanol/NR4OH (200:10:1) to give the title compound (7) as an off-white solid (2.60 g, 98%). 1H NMR (400 MHz, DMSO-d6) δ 9.86 (1H, s), 9.28 (1H, s), 9.01 (1H, s), 8.68 (1H, br s), 8.45 (1H, d, J=4 Hz), 8.23 (1 H, d, J=8 Hz), 8.10 (1H, d, J=4 Hz), 8.04 (1H, d, J=8 Hz), 7.54 (1H, dd, J=8 Hz, J=4 Hz), 5.43 (1H, p, J=8 Hz), 3.35 (4H, m), 3.26 (4H, m), 2.40 (2H, m), 2.03-2.10 (4H, m), 1.78 (2H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 415.1, Calculated 415.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography on silica gel eluting with CH2Cl2/methanol/NR4OH (200:10:1)

Sources & evidence

ORD record
ord-df2ec6f154244703b6ec7d5a9dd784d6
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

Loading…