[2-chloro-5-(2H-pyrazol-3-yl)-pyrimidin-4-yl]-(3-morpholin-4-yl-propyl)-amine → (RS)-N-(isopropylcarbamoyl)-S-(4-{4-(3-morpholin-4-yl-propylamino)-5-(2H-pyrazol-3-yl)-pyrimidin-2-ylamino}phenyl)-S-methylsulfoximide

HRID 1169782Notes

Reaction equation

HRID 1169782 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]([C:18]2[NH:19][N:20]=[CH:21][CH:22]=2)=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:39])(=[N:32][C:33](=[O:38])[NH:34][CH:35]([CH3:37])[CH3:36])=[O:31])=[CH:26][CH:25]=1>>[CH:35]([NH:34][C:33]([N:32]=[S:30]([C:27]1[CH:26]=[CH:25][C:24]([NH:23][C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[C:5]([C:18]3[NH:19][N:20]=[CH:21][CH:22]=3)=[CH:4][N:3]=2)=[CH:29][CH:28]=1)([CH3:39])=[O:31])=[O:38])([CH3:37])[CH3:36]

Participants

3

Reactant 2

HCID 58985683[2-chloro-5-(2H-pyrazol-3-yl)-pyrimidin-4-yl]-(3-morpholin-4-yl-propyl)-amineHCID 59550859HCID 59550859, compound

Product 1

HCID 58985642(RS)-N-(isopropylcarbamoyl)-S-(4-{4-(3-morpholin-4-yl-propylamino)-5-(2H-pyrazol-3-yl)-pyrimidin-2-ylamino}phenyl)-S-methylsulfoximideYield 34%

Procedure

In the reaction of [2-chloro-5-(2H-pyrazol-3-yl)-pyrimidin-4-yl]-(3-morpholin-4-yl-propyl)-amine (212.8 mg, 0.66 mmol) with (RS)—S-(4-aminophenyl)-N-(isopropylcarbamoyl)-S-methylsulphoximide (153 mg, 0.6 mmol) according to procedure 5c, the desired product is obtained in 34% yield (109 mg) after chromatographic purification (silica gel, dichloromethane/ethanol (0%-20% ethanol)).

Sources & evidence

ORD record
ord-cdc4dec0756b433885455ff7942d0877
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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