Water → HCID 58392278, compound

HRID 561621Notes

Reaction equation

[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][C:11]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)([CH:24]1[CH2:26][CH2:25]1)[C:12]1[C:20]2[C:15](=[C:16]([CH2:21][S:22][CH3:23])[CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)(=O)=O.O>CS(C)=O>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:11]([CH:24]2[CH2:25][CH2:26]2)([C:12]2[C:20]3[C:15](=[C:16]([CH2:21][S:22][CH3:23])[CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:9][C:1]#[N:2])=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 80 °C

Procedure

16 mg (0.25 mmol) of potassium cyanide were added to 57 mg (0.12 mmol) of the compound from Example 116A in 1 ml of DMSO. The mixture was stirred at 80° C. for 16 h, water was added to the reaction solution, and the crude product was purified directly by preparative HPLC (mobile phase: acetonitrile/water gradient). 29 mg (60% of theory) of the target compound were obtained.

Workup

customthe crude product was purified directly by preparative HPLC (mobile phase: acetonitrile/water gradient)
custom29 mg (60% of theory) of the target compound were obtained

Sources & evidence

ORD record: ord-4fc4d9de78424ef6a44c7106ecb26f39
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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