4-Methylmorpholine → Tert-butyl 6-[[2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetyl]amino]pyridine-3-carboxylate

HRID 524429Notes

Reaction equation

HRID 524429 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[C:14](O)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[C:26]([O:30][C:31]([C:33]1[CH:34]=[N:35][C:36]([NH2:39])=[CH:37][CH:38]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27].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:8]=[CH:9][C:10]([CH:13]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[C:14]([NH:39][C:36]3[N:35]=[CH:34][C:33]([C:31]([O:30][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:32])=[CH:38][CH:37]=3)=[O:15])=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22054350Tert-butyl 6-aminopyridine-3-carboxylateHCID 681825192-(4-Cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetic acid

Product 1

HCID 68182771Tert-butyl 6-[[2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetyl]amino]pyridine-3-carboxylateYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of example A8 was obtained by similar method described in example A1 using 2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetic acid (Preparation 3, 0.150 g, 0.408 mmol), 6-aminopyridine-3-carboxylic acid tert-butyl ester (preparation 54, 0.095 g, 0.49 mmol), HOBT (0.082 g, 0.612 mmol), and EDCl (0.116 g, 0.612 mmol), N-methyl morpholine (0.103 g, 1.02 mmom) in DCM (4 mL) to provide the title compound (0.031 g).

Sources & evidence

ORD record
ord-866b6d1bfe3f457b80f6b5f1f2d34a40
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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