4-Methylmorpholine → 2-(4-Cyclopropanesulfonyl-phenyl)-N-(5-isopropoxy-thiazolo[5,4-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yloxy)-acetamide

HRID 1889200Notes

Reaction equation

HRID 1889200 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:14](O)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH:24]([O:27][C:28]1[N:33]=[C:32]2[S:34][C:35]([NH2:37])=[N:36][C:31]2=[CH:30][CH:29]=1)([CH3:26])[CH3:25].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CN1CCOCC1>CN(C=O)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:14]([NH:37][C:35]3[S:34][C:32]4[C:31]([N:36]=3)=[CH:30][CH:29]=[C:28]([O:27][CH:24]([CH3:26])[CH3:25])[N:33]=4)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59610020(4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acidHCID 866482875-Isopropoxythiazolo[5,4-b]pyridin-2-amine

Product 1

HCID 596100592-(4-Cyclopropanesulfonyl-phenyl)-N-(5-isopropoxy-thiazolo[5,4-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yloxy)-acetamideYield 38.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of example A82 was obtained by similar method described in example A75 using (4-cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid (Preparation 14) (0.100 g,0.29 mmol), 5-iso-propoxy-thiazolo[5,4-b]pyridin-2-ylamine (0.067 g, 0.32 mmol), HOBt (0.047 g, 0.35 mmol), and EDCI (0.067 g, 0.35 mmol), N-methyl morpholine (0.065 g, 0.58 mmol) in DMF (5 mL) to provide the title compound (0.060 g).

Workup

  1. customwas obtained by similar method

Sources & evidence

ORD record
ord-0dc2c529a7eb4174a5dccc5df1012426
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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