Boron tribromide → HCID 136499147, compound

HRID 1524058Notes

Reaction equation

HRID 1524058 reaction equation
C(NS(C1C=CC=CC=1B(O)O)(=O)=O)(C)(C)C.BrC1C=CC(C2N=CC(N)=NC=2)=C(OC)C=1.[NH2:34][C:35]1[N:36]=[CH:37][C:38]([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[C:48]([S:53]([NH:56]C(C)(C)C)(=[O:55])=[O:54])=[CH:49][CH:50]=[CH:51][CH:52]=3)=[CH:43][C:42]=2[O:61]C)=[N:39][CH:40]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:34][C:35]1[N:36]=[CH:37][C:38]([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[C:48]([S:53]([NH2:56])(=[O:55])=[O:54])=[CH:49][CH:50]=[CH:51][CH:52]=3)=[CH:43][C:42]=2[OH:61])=[N:39][CH:40]=1

Participants

6

Reactant 4

HCID 25134Boron tribromideHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-HCID 90312903HCID 90312903, compoundHCID 90313768HCID 90313768, compound

Product 1

HCID 136499147HCID 136499147, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a manner similar to that described in Example 589 using (2-(N-(tert-butyl)sulfamoyl)phenyl)boronic acid and 5-(4-bromo-2-methoxyphenyl)pyrazin-2-amine. After the coupling, the tert-butyl group and methyl group were removed by treating a solution consisting of 4′-(5-aminopyrazin-2-yl)-N-(tert-butyl)-3′-methoxy-[1,1′-biphenyl]-2-sulfonamide (48 mg, 0.12 mmol) and DCM (2 mL), with BBr3 (0.14 mL, 1 M in DCM) at −78° Celsius. The reaction mixture was warmed to room temperature. After the starting material was consumed the reaction mixture was poured into saturated NH4Cl (10 mL) and extracted with DCM (3×10 mL). The combined organic extracts were dried with sodium sulfate, filtered, and concentrated to dryness. The resultant residue was subjected to HPLC purification to provide the title compound. MS (ESI): mass calcd. for C16H14N4O3S, 342.38; m/z found, 343.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.71 (s, 1H), 8.18 (dd, J=7.9, 1.4, 1H), 7.93 (d, J=1.4, 1H), 7.80 (d, J=8.2, 1H), 7.64-7.57 (m, 1H), 7.57-7.48 (m, 1H), 7.39 (dd, J=7.6, 1.3, 1H), 7.12 (dd, J=8.1, 1.9, 1H), 7.09-7.03 (m, 1H), 4.38 (s, 2H).

Workup

  1. customThe title compound was prepared in a manner similar to
  2. customAfter the coupling, the tert-butyl group and methyl group were removed
  3. additionby treating a solution
  4. customAfter the starting material was consumed the reaction mixture
  5. additionwas poured into saturated NH4Cl (10 mL)
  6. extractionextracted with DCM (3×10 mL)
  7. dry with materialThe combined organic extracts were dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe resultant residue was subjected to HPLC purification

Sources & evidence

ORD record
ord-3c66333640fd4d8dbd475fb46a9bf8a9
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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