Hydrochloric Acid → HCID 131735815, compound

HRID 2205559Notes

Reaction equation

HRID 2205559 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=4)=[O:19])=[CH:13][C:11]=3[CH:12]=2)=[CH:6][C:5]([B:28]2[O:32]C(C)(C)C(C)(C)[O:29]2)=[CH:4][N:3]=1.Cl>O1CCCC1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([B:28]([OH:29])[OH:32])=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=3)=[O:19])=[CH:13][C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131735813HCID 131735813, compound

Product 1

HCID 131735815HCID 131735815, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 1-{2-[2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]-1-benzothien-5-yl}-3-(3-methylphenyl)urea (500 mg, 1 mmol, 1 eq) in tetrahydrofuran (6 mL) at room temperature was added dropwise aqueous HCl (3N, 6 mL) and the reaction was stirred at room temperature for 4 hours. The reaction mixture was filtered directly through a Buchner funnel, rinsed with isopropanol, followed by i-PrOH—H2O (1:1) to give {6-amino-5-[5-({[(3-methylphenyl)amino]carbonyl}amino)-1-benzothien-2-yl]pyridin-3-yl}boronic acid as a white solid in amount of 384 mg.

Workup

  1. filtrationThe reaction mixture was filtered directly through a Buchner funnel
  2. washrinsed with isopropanol

Sources & evidence

ORD record
ord-5416e0daa96646a18a9eb7bbbf6c0ed0
Source dataset
uspto-grants-2016_06
Patent number
US09371314B2

Reaction notes

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