Hydrochloric Acid → HCID 178521949, compound

HRID 2383480Notes

Reaction equation

HRID 2383480 reaction equation
[C:1]1([NH:7][C:8]([N:10]2[CH2:19][C:18]3[CH:17]=[N:16][C:15]4[NH:20][N:21]=[C:22]([C:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH:24]=5)[C:14]=4[C:13]=3[CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:36]>ClCCl.O1CCOCC1>[Cl-:36].[C:1]1([NH:7][C:8]([N:10]2[CH2:19][C:18]3[CH:17]=[N:16][C:15]4[NH:20][N:21]=[C:22]([C:23]5[CH2:28][CH2:27][NH2+:26][CH2:25][CH:24]=5)[C:14]=4[C:13]=3[CH2:12][CH2:11]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178451822HCID 178451822, compound

Product 1

HCID 178521949HCID 178521949, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(7-(phenylcarbamoyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-1-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.06 g, 0.12 mmol) was dissolved in dichloromethane (5 mL) and 4M HCl in 1,4-dioxane (0.5 mL) was added and stirred till complete as observed by LCMS. The reaction mixture was then evaporated in vacuo. (0.04 g, 80%). M.p.=230-231° C.; 400 MHz 1H NMR (DMSO-d6) δ: 9.35 (br s, 2H), 8.78 (s, 1H), 8.36 (s, 1H), 7.52-7.49 (d, J=7.4 Hz, 2H), 7.24-7.22 (t, J=7.8 Hz, 2H), 6.96-6.92 (t, J=7.4 Hz, 1H), 6.05 (s, 1H), 4.82 (s, 2H), 3.78-3.74 (m, 5H), 3.36-3.35 (br s, 2H), 3.18 (t, J=6 Hz, 2H), 2.77 (br s, 2H); LCMS [M+H]: 375.

Workup

  1. customThe reaction mixture was then evaporated in vacuo

Sources & evidence

ORD record
ord-e7283171aaf94bd3b0cc66daaecb09ea
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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