Boron tribromide → HCID 135921361, compound

HRID 2189208Notes

Reaction equation

HRID 2189208 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[C:14]1[N:23]=[C:22]([NH:24][C@H:25]2[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1>ClCCl>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]([OH:6])=[C:8]([C:14]2[N:23]=[C:22]([NH:24][C@H:25]3[CH2:29][CH2:28][NH:27][CH2:26]3)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67366556HCID 67366556, compound

Product 1

HCID 135921361HCID 135921361, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (0.454 mL of a 1 M solution in dichloromethane, 0.45 mmol) was added to a solution of (S)-tert-butyl 3-(2-(2-methoxy-5-methylphenyl)quinazolin-4-ylamino)pyrrolidine-1-carboxylate (0.079 g, 0.23 mmol) in dichloromethane (2.3 mL). After 16 hours, the reaction was quenched by the addition of methanol (2 mL). Hydrochloric acid (1.5 mL of a 4 M solution in dioxane) was added and the mixture was heated at reflux for 6 hours. The solution was cooled, concentrated, and purified by SCX-2 Isolute column (2 g), eluting first with methanol and finally 1 M ammonia in methanol. Silica column chromatography (5% methanol in DCM) gave the title compound as a yellow solid (0.025 g, 35%).

Workup

  1. customthe reaction was quenched by the addition of methanol (2 mL)
  2. additionHydrochloric acid (1.5 mL of a 4 M solution in dioxane) was added
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 6 hours
  5. temperatureThe solution was cooled
  6. concentrationconcentrated
  7. custompurified by SCX-2 Isolute column (2 g)
  8. washeluting first with methanol and finally 1 M ammonia in methanol

Sources & evidence

ORD record
ord-3f01057988514f3493714d80c0cd4513
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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