Boron tribromide → HCID 86656651, compound

HRID 882907Notes

Reaction equation

HRID 882907 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[NH2:8][C:9]1[C:10]([C:17]([NH:19][CH2:20][C@@H:21]([N+:25]([CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37]C)=[CH:33][CH:32]=2)([CH3:27])[CH3:26])[CH2:22][CH2:23][CH3:24])=[O:18])=[N:11][C:12]([Cl:16])=[C:13]([NH2:15])[N:14]=1.B(Br)(Br)Br>C(Cl)Cl.CCCCCCC>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[NH2:8][C:9]1[C:10]([C:17]([NH:19][CH2:20][C@@H:21]([N+:25]([CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)([CH3:27])[CH3:26])[CH2:22][CH2:23][CH3:24])=[O:18])=[N:11][C:12]([Cl:16])=[C:13]([NH2:15])[N:14]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 44548148HCID 44548148, compound

Product 1

HCID 86656651HCID 86656651, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

To a solution of ((S)-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-[3-(4-methoxy-phenyl)-propyl]-dimethyl-ammonium trifluoroacetate (Example 120) (313 mg, 0.556 mmol) in DCM (100 mL) is added BBr3 (3.34 mL of a 1M solution in heptane, 3.34 mmol). The reaction mixture is stirred at RT overnight. The reaction mixture is quenched cautiously by the addition of water then the organic solvents are removed in vacuo. Purification by reverse phase column chromatography (Isolute™ C18, 0-50% acetonitrile in water with 0.1% TFA) affords the title compound. M+ 435. 1H NMR (400 MHz, DMSO-d6) δ 8.40 (1H, t), 7.13 (2H, br), 6.89 (2H, d), 6.64 (2H, d), 5.29 (3H, br), 3.79-3.68 (1H, m), 3.57-3.43 (3H, m), 3.37-3.25 (1H, m), 3.04 (3H, s), 3.01 (3H, s), 2.41-2.30 (2H, m), 1.95-1.73 (3H, m), 1.64-1.35 (3H, m), 0.92 (3H, t).

Workup

  1. customThe reaction mixture is quenched cautiously by the addition of water
  2. customthe organic solvents are removed in vacuo
  3. customPurification by reverse phase column chromatography (Isolute™ C18, 0-50% acetonitrile in water with 0.1% TFA)

Sources & evidence

ORD record
ord-0ece3a8cdc704fb2915401522a517309
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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