Hydrochloric Acid → HCID 178520261, compound

HRID 1011309Notes

Reaction equation

HRID 1011309 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:29]=[CH:28][N:27]=[C:26]4[C:22]=3[N:23]=[CH:24][N:25]4C3CCCCO3)=[CH:16][CH:15]=2)=[S:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CCOCC>O1CCOCC1>[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:29]=[CH:28][N:27]=[C:26]4[C:22]=3[N:23]=[CH:24][NH:25]4)=[CH:18][CH:19]=2)=[S:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11554915HCID 11554915, compound

Product 1

HCID 178520261HCID 178520261, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 2-phenyl-N-{[(4-{[9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl]oxy}phenyl)-amino]carbonothioyl}acetamide (190 mg, 0.38 mmol) in 30 mL of dioxane was added 3 mL of 4N HCl in dioxane and let to stir for 1 h. On concentration of the reaction mixture and trituration with ether yielded 2-phenyl-N-({[4-(9H-purin-6-yloxy)phenyl]amino}carbonothioyl)acetamide (102 mg, 65% yield) as a colorless solid. 1H NMR (400 MHz, DMSO d6): δ 12.40 (s, 1H), 11.80 (s, 1H), 8.6 (s, 1H), 8.4 (s, 1H), 7.70 (m, 2H), 7.35 (m, 7H), 3.8 (s, 2H). MS (ESI) for C20H16N6O2S: 433 (MH+).

Sources & evidence

ORD record
ord-5150496a247740c1b6977ba22639c71a
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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