Hydrochloric Acid → HCID 25242487, compound

HRID 1926638Notes

Reaction equation

HRID 1926638 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[N:21]=[C:20]([N:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)[CH:19]=[N:18][CH:17]=4)=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1.Cl>O1CCOCC1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[CH:17]=[N:18][CH:19]=[C:20]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)[N:21]=4)=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57502416HCID 57502416, compound

Product 1

HCID 25242487HCID 25242487, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-butyl 4-{6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrazin-2-yl}piperazine-1-carboxylate (0.047 g, 0.10 mmol) was suspended in dioxane (1.0 ml). 4M HCl in dioxane (1.0 ml) was added, and the reaction mixture was stirred at room temperature for 45 min. The reaction mixture was filtered to afford 5-(1-methyl-1H-pyrazol-4-yl)-3-(6-piperazin-1-ylpyrazin-2-yl)-1H-pyrrolo[2,3-b]pyridine as an orange/yellow solid (hydrochloride salt). 1H NMR (600 MHz, DMSO-D6) 12.4 (br s, 1H); 9.41 (br s, 2H); 8.71 (br d, 1H); 8.56 (s, 1H); 8.55 (d, 1H); 8.39 (d, 1H); 8.19 (s, 1H); 8.18 (s, 1H); 7.89 (s, 1H); 3.93 (br t, 4H); 3.87 (s, 3H); 3.25 (br m, 4H). LRMS calculated for C19H20N8 [M+H]+, 361.2; found 361.2.

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-2aa3c08e10bf44bc9d876d1a95d45627
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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