(3-Acetamidophenyl)boronic acid → HCID 59593160, compound

HRID 2262228Notes

Reaction equation

HRID 2262228 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[C:13]4[CH:18]=[C:17]([C:19]([OH:21])=O)SC=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[C:28]([NH:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)(=[O:30])[CH3:29]>>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[C:13]4[O:21][C:19]([C:34]5[CH:33]=[C:32]([NH:31][C:28](=[O:30])[CH3:29])[CH:37]=[CH:36][CH:35]=5)=[CH:17][C:18]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

3

Reactant 2

HCID 157274(3-Acetamidophenyl)boronic acidHCID 595928852-(1H-indazol-4-yl)-4-morpholinothieno[2,3-d]pyrimidine-6-carboxylic acid

Product 1

HCID 59593160HCID 59593160, compound

Procedure

2-Chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine 45 from Example 27 was reacted with 3-acetamidophenylboronic acid via General Procedure A to give the corresponding intermediate, after purification by flash chromatography, which was then reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 to give, after purification by reverse phase HPLC, 341. MS (Q1) 455 (M+)

Workup

  1. customto give the corresponding intermediate
  2. customafter purification by flash chromatography, which
  3. customwas then reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7
  4. customto give
  5. customafter purification by reverse phase HPLC, 341

Sources & evidence

ORD record
ord-a9a976ef4fde4c638dffe93a69f4e22b
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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