Hydrochloric Acid → 3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one hydrochloride

HRID 634407Notes

Reaction equation

HRID 634407 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[O:15][C:16](=[O:37])[C:17]4[C:22]([C:23]=3[C:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH:25]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH3:13])[N:9]=[C:10]([I:11])[C:3]=12.[ClH:38]>O1CCOCC1>[ClH:38].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[O:15][C:16](=[O:37])[C:17]4[C:22]([C:23]=3[C:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH:25]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH3:13])[N:9]=[C:10]([I:11])[C:3]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118131159Tert-butyl 4-(3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 1181311443-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Tert-butyl 4-(3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate D14, 1.5 g, 2.441 mmol) was suspended in 1,4-Dioxane (5 ml) and 4 M HCl in dioxane (15.26 ml, 61.0 mmol) was added. The mixture was stirred at rt for 4 h, then volatiles were removed under reduced pressure to give title compound (1.56 g) as a light pink powder.

Workup

  1. customvolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-f718ab62e42442c2bcf7d5ee0c2d1fae
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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