Triethylamine → 3-{[[4-(BOC-methyl-amino)-cyclohexyl]-(3-chloro-benzo[b]thiophene-2-carbonyl)-amino]-methyl}-4-ethoxy-benzene boronic acid

HRID 2389567Notes

Reaction equation

HRID 2389567 reaction equation
[C:1]([N:8]([CH3:29])[CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][CH2:16][C:17]2[CH:18]=[C:19]([B:26]([OH:28])[OH:27])[CH:20]=[CH:21][C:22]=2[O:23][CH2:24][CH3:25])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[Cl:37][C:38]1[C:39]2[CH:49]=[CH:48][CH:47]=[CH:46][C:40]=2[S:41][C:42]=1[C:43](Cl)=[O:44]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([N:8]([CH3:29])[CH:9]1[CH2:10][CH2:11][CH:12]([N:15]([CH2:16][C:17]2[CH:18]=[C:19]([B:26]([OH:27])[OH:28])[CH:20]=[CH:21][C:22]=2[O:23][CH2:24][CH3:25])[C:43]([C:42]2[S:41][C:40]3[CH:46]=[CH:47][CH:48]=[CH:49][C:39]=3[C:38]=2[Cl:37])=[O:44])[CH2:13][CH2:14]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chlorideHCID 596835893-{[4-(BOC-methyl-amino)-cyclohexylamino]-methyl}-4-ethoxy-benzene boronic acid

Product 1

HCID 596834943-{[[4-(BOC-methyl-amino)-cyclohexyl]-(3-chloro-benzo[b]thiophene-2-carbonyl)-amino]-methyl}-4-ethoxy-benzene boronic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of boronic acid 11 (700 mg, 1.72 mmol) in DCM (15 mL) at 0° C. is treated with triethylamine (0.48 mL, 3.45 mmol), followed by 3-chlorobenzo-[b]thiophene-2-carbonyl chloride (439 mg, 1.90 mmol) in one portion. After warming to RT, the solution is stirred 16 h. Analysis by LC/MS at this juncture confirmed the reaction is complete. Thus the reaction is diluted with aqueous NaHCO3 (20 mL) and extracted into EtOAc (3×25 mL). The combined EtOAc phases are dried (Na2SO4) and reduced in vacuo to afford the title compound.

Workup

  1. extractionextracted into EtOAc (3×25 mL)
  2. dry with materialThe combined EtOAc phases are dried (Na2SO4)

Sources & evidence

ORD record
ord-0e99be62bb854970a8066fff2f873e0d
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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