4-((5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)morpholine → Methyl 4-[[2-amino-5-[5-(morpholinomethyl)-2-thienyl]pyridine-3-carbonyl]amino]pyridine-3-carboxylate

HRID 919235Notes

Reaction equation

HRID 919235 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[C:17]([O:19][CH3:20])=[O:18])=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[N:22]1([CH2:28][C:29]2[S:33][C:32](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:30]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[CH3:20][O:19][C:17](=[O:18])[C:12]1[C:11]([NH:10][C:8]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:32]3[S:33][C:29]([CH2:28][N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)=[CH:30][CH:31]=3)[CH:6]=2)=[O:9])=[CH:16][CH:15]=[N:14][CH:13]=1

Participants

3

Reactant 2

HCID 467390464-((5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)morpholineHCID 71061375Methyl 4-[(2-amino-5-bromo-pyridine-3-carbonyl)amino]pyridine-3-carboxylate

Product 1

HCID 71060833Methyl 4-[[2-amino-5-[5-(morpholinomethyl)-2-thienyl]pyridine-3-carbonyl]amino]pyridine-3-carboxylate

Procedure

Reaction of methyl 4-[(2-amino-5-bromo-pyridine-3-carbonyl)amino]pyridine-3-carboxylate with 5-(4-morpholinylmethyl)thiophene-2-boronic acid pinacol ester gives compound “A35”; HPLC/MS: 1.36 min, [M+H]=454;

Workup

  1. customgives compound “A35”
  2. custom1.36 min, [M+H]=454

Sources & evidence

ORD record
ord-d86ea79b5ee040b2b6d8d2441674332f
Source dataset
uspto-grants-2016_03
Patent number
US09273029B2

Reaction notes

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