Boron tribromide → HCID 135723770, compound

HRID 533213Notes

Reaction equation

HRID 533213 reaction equation
C(OC[N:10]1[C:18]2[C:17]([O:19]C)=[N:16][CH:15]=[N:14][C:13]=2[C:12]([CH2:21][NH:22][C@@H:23]([CH2:28][OH:29])[C@@H:24]([OH:27])[CH2:25][OH:26])=[CH:11]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl.CO>[OH:29][CH2:28][C@H:23]([NH:22][CH2:21][C:12]1[C:13]2[N:14]=[CH:15][NH:16][C:17](=[O:19])[C:18]=2[NH:10][CH:11]=1)[C@@H:24]([OH:27])[CH2:25][OH:26]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 25223391HCID 25223391, compound

Product 1

HCID 135723770HCID 135723770, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product from Example 18.2 (0.056 g, 0.14 mmol) in DCM (7 ml) at −78° C. was added boron tribromide (1.39 ml, 1.39 mmol, 1.0M in DCM). After 15 mins the reaction mixture was warmed to ambient temperature and coevaporated with methanol (3×). The residue was stirred in methanol (7N ammonia solution) for 10 mins and evaporated on to silica gel. The material was chromatographed on silica gel (chloroform-methanol-conc. ammonia, 10:9:1) giving a white solid (17 mg, 46%). 1H NMR (D2O) δ 8.03 (s, 1H), 7.59 (s, 1H), 4.41 (ABq, 2H), 3.88 (dd, J=13.2, 4.2 Hz, 1H), 3.80 (m, 1H), 3.72 (dd, J=13.2, 5.3 Hz, 1H), 3.60 (dd, J=12.5, 3.4 Hz, 2H), 3.47 (dd, J=12.5, 4.5 Hz, 1H), 3.26 (m, 1H). +ESMS found 269.1262 (M+H)+ C11H17N4O4 requires 269.1250.

Workup

  1. customevaporated on to silica gel
  2. customThe material was chromatographed on silica gel (chloroform-methanol-conc. ammonia, 10:9:1)

Sources & evidence

ORD record
ord-6436a920cd614cc7ab9d3140affc3232
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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