Trifluoroacetic acid → Ethyl (4-((6-((9-cyclopentyl-9 H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-pyridinyl)methyl)-1-piperazinyl)acetate

HRID 876031Notes

Reaction equation

HRID 876031 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]1([N:13]2[C:17]3[N:18]=[C:19]([NH2:22])[N:20]=[CH:21][C:16]=3[C:15]3[CH:23]=[CH:24][N:25]=[CH:26][C:14]2=3)[CH2:12][CH2:11][CH2:10][CH2:9]1.Cl[C:28]1[N:33]=[CH:32][C:31]([CH2:34][N:35]2[CH2:40][CH2:39][N:38]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:37][CH2:36]2)=[CH:30][CH:29]=1>>[CH:8]1([N:13]2[C:17]3[N:18]=[C:19]([NH:22][C:28]4[N:33]=[CH:32][C:31]([CH2:34][N:35]5[CH2:36][CH2:37][N:38]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:39][CH2:40]5)=[CH:30][CH:29]=4)[N:20]=[CH:21][C:16]=3[C:15]3[CH:23]=[CH:24][N:25]=[CH:26][C:14]2=3)[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 582995859-Cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amineHCID 58300204Ethyl 2-(4-((6-chloropyridin-3-yl)methyl)piperazin-1-yl)acetate

Product 1

HCID 58299758Ethyl (4-((6-((9-cyclopentyl-9 H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-pyridinyl)methyl)-1-piperazinyl)acetate

Procedure

Compound 347 was prepared as an off-white solid (TFA salt) from compound 4 and compound 348 using chemistry similar to that described in example 200. 1H NMR (500 MHz, CD3OD) δ ppm 9.57 (1 H, s), 9.27 (1 H, s), 8.60 (2 H, s), 8.47 (1 H, d, J=2.0 Hz), 8.32-8.43 (1 H, m), 8.07 (1 H, dd, J=8.8, 2.2 Hz), 5.46 (1 H, dq, J=9.0, 8.9 Hz), 4.12-4.28 (4 H, m), 3.65 (2 H, br. s.), 2.96-3.21 (8 H, m), 2.48-2.61 (2 H, m), 2.15-2.31 (4 H, m), 1.85-1.99 (2 H, m), 1.28 (3 H, t, J=7.2 Hz). LCMS-ESI (POS), M/Z, M+1: Found 515.2.

Sources & evidence

ORD record
ord-8f88a5fba72e43af92feef3e149cf3dc
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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