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4-amino-N-(1-methoxypropan-2-yl)benzene-1-sulfonamide → 4-[[4-[(2,6-Dimethyl-3-pyridinyl)oxy]-2-pyridinyl]amino]-N-(2-methoxy-1-methylethyl)benzenesulfonamide

HRID 470
Notes
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Reaction equation

HRID 470 reaction equation
COCC(C)NS(=O)(=O)c1ccc(N)cc1.Cc1ccc(Oc2ccnc(Cl)c2)c(C)n1>CC(=O)N(C)C.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>COCC(C)NS(=O)(=O)c1ccc(Nc2cc(Oc3ccc(C)nc3C)ccn2)cc1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 50195684-amino-N-(1-methoxypropan-2-yl)benzene-1-sulfonamideHCID 445982003-(2-Chloropyridin-4-yl)oxy-2,6-dimethyl-pyridine

Product 1

HCID 689421304-[[4-[(2,6-Dimethyl-3-pyridinyl)oxy]-2-pyridinyl]amino]-N-(2-methoxy-1-methylethyl)benzenesulfonamideYield 51.97%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagent
HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Catalyst
HCID 4144353Palladium (II) acetateCatalyst
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

In a 10 mL microwave reactor 3-(2-chloropyridin-4-yloxy)-2,6-dimethylpyridine (100 mg, 0.43 mmol) and 4-amino-N-(1-methoxypropan-2-yl)benzenesulfonamide (104 mg, 0.43 mmol) were dissolved in DMA (3 mL) to give a brown solution.To the resultant solution Cesium carbonate (0.068 mL, 0.85 mmol) was added and sparged with nitrogen for 1 minute. Then Palladium(II) acetate (6.70 mg, 0.03 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (29.6 mg, 0.05 mmol) were added and the reaction mixture was sealed. The reaction was heated to150 °C for 25 minutes in the biotage microwave.The reaction was cooled to room temperature and LCMS shows reaction was completed. Reaction mixture was filtered through Celite Bed and washed with Dichloromethane. Filtrate was subjected to concentration to get DMA solution which was given to analytical department to purify using Mass based HPLC. After purification compound was isolated to get pale yellow solid of 4-(4-(2,6-dimethylpyridin-3-yloxy)pyridin-2-ylamino)-N-(1-methoxypropan-2-yl)benzenesulfonamide (98 mg, 52.0 %)

Sources & evidence

ORD record
ord-067637c197bb4672875d64a38b7940ee
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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