4-Methylmorpholine → Methyl 2-[[2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetyl]amino]-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate

HRID 524427Notes

Reaction equation

HRID 524427 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]([OH:16])=O)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH2:24]([O:26][C:27]([CH:29]1[CH2:38][CH2:37][C:32]2[N:33]=[C:34]([NH2:36])[S:35][C:31]=2[CH2:30]1)=[O:28])C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.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:36][C:34]3[S:35][C:31]4[CH2:30][CH:29]([C:27]([O:26][CH3:24])=[O:28])[CH2:38][CH2:37][C:32]=4[N:33]=3)=[O:16])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15101101Ethyl 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylateHCID 59610020(4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid

Product 1

HCID 86669556Methyl 2-[[2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetyl]amino]-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylateYield 41.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of example A6 was obtained by similar method described in example A1 using 2-(4-cyclopropanesulfonyl-phenyl)-2-[(tetrahydro-pyran-4-yloxy)]-acetic acid (Preparation 4, 0.340 g, 1.0 mmol), 2-Amino-4,5,6,7-tetrahydro-benzothiazole-6-carboxylic acid ethyl ester (Preparation 49; 0.286 g, 1.0 mmol), HOBt (0.162 g, 1.2 mmol), and EDCl (0.229 g, 1.2 mmol), N-methyl morpholine (0.36 g, 3.58 mmol) in DMF (6 mL) to provide the title compound (0.22 g).

Sources & evidence

ORD record
ord-c0502fac0a694378a953d9730e9a488e
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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