Sodium Chloride → HCID 58985534, compound

HRID 1169798Notes

Reaction equation

[CH2:1]([N:8]1[N:12]=[N:11][C:10]([C:13]2[C:14]([NH:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[N:15][C:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:34])(=[N:28]C(OCC)=O)=[O:27])=[CH:22][CH:21]=3)=[N:17][CH:18]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])C.[Na+].[Na+].[Cl-]>C(O)C>[CH2:1]([N:8]1[N:12]=[N:11][C:10]([C:13]2[C:14]([NH:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[N:15][C:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:34])(=[NH:28])=[O:27])=[CH:22][CH:21]=3)=[N:17][CH:18]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

28 mg (0.048 mmol) (RS)—S-(4-{[5-(2-benzyl-2H-tetrazol-5-yl)-4-(cyclohexyl-amino)pyrimidine-2-yl]amino}phenyl)-N-(ethoxycarbonyl)-S-methylsulfoximide in 0.4 ml ethanol are treated with 78 μL (0.119 mmol) of a freshly prepared 1.53 molar sodium ethanolate solution and stirred for 22 hours at 60° C. Next, a further 0.15 ml (0.229 mmol) of the 1.53 molar sodium ethanolate solution is added, and the mixture stirred for a further 22 hours at 60° C. The mixture is treated with saturated NaCl solution and extracted with ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated. 24 mg (0.048 mmol, corresponding to 100% of theor.) of the product is obtained.

Workup

stirringthe mixture stirred for a further 22 hours at 60° C
extractionextracted with ethyl acetate
dry with materialThe combined organic phases are dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
custom24 mg (0.048 mmol, corresponding to 100% of theor.) of the product is obtained

Sources & evidence

ORD record: ord-c1119e5e412641ccac49c88c5ec0daae
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825128B2

Reaction notes

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