Hydrochloric Acid → 9-cyclopentyl-N-(5-(1-piperazinylcarbonyl)-2-pyridinyl)-9 H-pyrido[4',3':4,5]-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 79210Notes

Reaction equation

HRID 79210 reaction equation
Cl.[CH:2]1([N:7]2[C:11]3[N:12]=[C:13]([NH2:16])[N:14]=[CH:15][C:10]=3[C:9]3[CH:17]=[CH:18][N:19]=[CH:20][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl[C:22]1[N:42]=[CH:41][CH:40]=[CH:39][C:23]=1[C:24]([N:26]1[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]1)=[O:25]>>[CH:2]1([N:7]2[C:11]3[N:12]=[C:13]([NH:16][C:41]4[CH:40]=[CH:39][C:23]([C:24]([N:26]5[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]5)=[O:25])=[CH:22][N:42]=4)[N:14]=[CH:15][C:10]=3[C:9]3[CH:17]=[CH:18][N:19]=[CH:20][C:8]2=3)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4321619tert-Butyl 4-(2-chloronicotinoyl)piperazine-1-carboxylateHCID 582995859-Cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 582996199-cyclopentyl-N-(5-(1-piperazinylcarbonyl)-2-pyridinyl)-9 H-pyrido[4',3':4,5]-pyrrolo[2,3-d]pyrimidin-2-amine

Procedure

Compound 350 was prepared as a light yellow solid (HCl salt) from compound 4 and compound 351 using chemistry similar to that described in example 200. 1H NMR (500 MHz, DMSO-d6) δ ppm 11.06 (1 H, br. s.), 9.70 (1 H, s), 9.47 (1 H, s), 9.39 (2 H, br. s.), 8.67-8.75 (2 H, m), 8.51 (1 H, d, J=1.7 Hz), 8.37 (1 H, d, J=8.6 Hz), 8.02 (1 H, dd, J=8.7, 2.3 Hz), 5.43 (1 H, dq, J=8.9, 8.8 Hz), 3.77 (4 H, br. s.), 3.18 (4 H, br. s.), 2.42-2.48 (2 H, m), 2.02-2.20 (4 H, m), 1.70-1.83 (2 H, m). LCMS-ESI (POS), M/Z, M+1: Found 443.2.

Sources & evidence

ORD record
ord-05778d573ab74a7e97fdda354f58170a
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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