Hydrochloric Acid → HCID 58299854, compound

HRID 79167Notes

Reaction equation

HRID 79167 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][C:37](=[O:40])[N:38]([CH3:39])[C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CO.C(OCC)C>O1CCOCC1>[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[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]5)=[CH:20][N:21]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][C:37](=[O:40])[N:38]([CH3:39])[C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3283Diethyl EtherHCID 58299974tert-Butyl 4-(6-((9-cyclopentyl-8-methyl-7-oxo-8,9-dihydro-7H-pyrido[3',2':4,5]-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-pyridinyl)-1-piperazinecarboxylate

Product 1

HCID 58299854HCID 58299854, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Compound 274 (51 mg) was dissolved in 2 mL dioxane. Dioxane (1 mL) saturated at room temperature with HCl was added, followed by 1 mL methanol to aid solution. The reaction was stirred at room temperature for 80 min. The solution was then added dropwise to diethyl ether (8 mL) and the resulting precipitate was collected and dried in vacuo to give compound 271 as a yellow solid (26 mg, 62%). 1H NMR (500 MHz, DMSO-d6) δ 11.75 (br. s., 1 H) 9.36 (br. s., 2 H) 9.20 (s, 1 H) 8.53 (d, J=8.31 Hz, 1 H) 7.91-8.01 (m, 2 H) 7.49 (d, J=9.29 Hz, 1 H) 6.83 (d, J=8.56 Hz, 1 H) 5.37 (quin, J=8.56 Hz, 1 H) 3.35-3.43 (m, 5 H) 1.94-2.13 (m, 4 H) 1.64-1.79 (m, 2 H) ppm.

Workup

  1. customthe resulting precipitate was collected
  2. customdried in vacuo

Sources & evidence

ORD record
ord-95475c638f2640dd990b93f9612f4d9d
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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