4-Methylmorpholine → Ethyl 1-[2-[[2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetyl]amino]thiazol-5-yl]pyrazole-4-carboxylate

HRID 524426Notes

Reaction equation

HRID 524426 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.[NH2:24][C:25]1[S:26][C:27]([N:30]2[CH:34]=[C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:32]=[N:31]2)=[CH:28][N:29]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CN1CCOCC1>C(Cl)Cl>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O:17][CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:14]([NH:24][C:25]3[S:26][C:27]([N:30]4[CH:34]=[C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:32]=[N:31]4)=[CH:28][N:29]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59610020(4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acidHCID 86669555Ethyl 1-(2-aminothiazol-5-yl)pyrazole-4-carboxylate

Product 1

HCID 86669554Ethyl 1-[2-[[2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetyl]amino]thiazol-5-yl]pyrazole-4-carboxylateYield 49.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of example A5 was obtained by similar method described in example A1 using 2-(4-cyclopropanesulfonyl-phenyl)-2-[(tetrahydro-pyran-4-yloxy)]-acetic acid (Preparation 4; 1.1 g, 3.23 mmol), ethyl 1-(2-aminothiazol-5-yl)pyrazole-4-carboxylate (Preparation 41; 0.924 g, 3.88 mmol), HOBt (0.524 g, 3.88 mmol), and EDCl (0.741 g, 3.88 mmol), N-methyl morpholine (0.815 g, 0.88 mmol) in DCM (20 mL) to provide the title compound (0.9 g).

Sources & evidence

ORD record
ord-03aab9f14eff4f0194639973388655ff
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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