2-phenyl-N-{[(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl) amino]carbonothioyl}acetamide → 2-phenyl-N-({[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]amino}carbonothioyl)acetamide

HRID 1011297Notes

Reaction equation

HRID 1011297 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[N:26]=[CH:25][N:24]=[C:23]4[N:27](C5CCCCO5)[N:28]=[CH:29][C:22]=34)=[CH:16][CH:15]=2)=[S:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O1CCOCC1>CCOCC>[C:1]1([CH2:7][C:8]([NH:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:21]3[N:26]=[CH:25][N:24]=[C:23]4[NH:27][N:28]=[CH:29][C:22]=34)=[CH:18][CH:19]=2)=[S:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 116916472-phenyl-N-{[(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl) amino]carbonothioyl}acetamideHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 117111522-phenyl-N-({[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]amino}carbonothioyl)acetamideYield 100.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 2-phenyl-N-{[(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl)amino]-carbonothioyl}acetamide (0.070 g, 0.14 mmol, 1.0 eq.) and 4M HCl/Dioxane (5 ml). After 5 minutes ether was added. The resulting solid was filtered and washed twice with ether. The solid was further dried under vacuum to give 2-phenyl-N-({[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]amino}carbonothioyl)acetamide (0.057 g, 96% yield). 1H NMR (400 MHz, DMSO): 12.40 (s, 1H), 11.79 (s, 1H), 8.52 (s, 1H), 8.14 (s, 1H), 7.71 (d, 2H), 7.33 (m, 8H), 3.83 (s, 2H); MS (ESI) for C20H16N6O2S: 403 (MH+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. filtrationThe resulting solid was filtered
  3. washwashed twice with ether
  4. customThe solid was further dried under vacuum

Sources & evidence

ORD record
ord-051b0c27af904a7f9fed4a23b694ee96
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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