Hydrochloric Acid → HCID 59674057, compound

HRID 1891055Notes

Reaction equation

HRID 1891055 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]#[CH:11])[C:5]([I:12])=[CH:4][N:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:28])(=[N:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:21])=[CH:16][CH:15]=1.Cl>C(#N)C.O1CCOCC1.O>[CH2:26]([O:25][C:23]([N:22]=[S:20]([C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:2]2[N:7]=[C:6]([NH:8][CH2:9][C:10]#[CH:11])[C:5]([I:12])=[CH:4][N:3]=2)=[CH:19][CH:18]=1)([CH3:28])=[O:21])=[O:24])[CH3:27]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 44122615Ethyl [(4-aminophenyl)(methyl)oxido-sulfanylidene]carbamateHCID 59674063HCID 59674063, compound

Product 1

HCID 59674057HCID 59674057, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

400 mg (1.65 mmol) of (2-chloro-5-iodopyrimidin-4-yl)-prop-2-in-1-yl-amine and 630 mg (2.15 mmol) of (RS)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-methyl sulfoximide in 7 ml of acetonitrile are mixed with 0.6 ml of a 4N solution of HCl in dioxane and 1 ml of water. The batch is stirred for 24 hours at 50° C. The solvent is drawn off, and the remaining residue is purified by chromatography (DCM/EtOH 9:1). 279 mg (0.56 mmol, corresponding to 54% of theory) of the product is obtained.

Workup

  1. customthe remaining residue is purified by chromatography (DCM/EtOH 9:1)
  2. custom279 mg (0.56 mmol, corresponding to 54% of theory) of the product is obtained

Sources & evidence

ORD record
ord-7bb6a77737a44efe9b46e065fa6e97c4
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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