Boron tribromide → HCID 178463543, compound

HRID 717849Notes

Reaction equation

HRID 717849 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:27]=[N:28][CH:29]=2)[C:5]([N:20]2[CH2:24][CH2:23][C@@H:22]([O:25]C)[CH2:21]2)=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][NH:15]3)[CH3:9])[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[N:4]([CH:27]=[N:28][CH:29]=2)[C:5]([N:20]2[CH2:24][CH2:23][C@@H:22]([OH:25])[CH2:21]2)=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][NH:15]3)[CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178496657HCID 178496657, compound

Product 1

HCID 178463543HCID 178463543, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of N-(1-{8-chloro-5-[(3R)-3-methoxypyrrolidin-1-yl]imidazo[1,5-a]pyridin-6-yl}ethyl)-9H-purin-6-amine (27.0 mg, 0.0654 mmol) in methylene chloride (1.0 mL) at −78° C. under an atmosphere of nitrogen was added slowly 1.0 M boron tribromide in methylene chloride (0.47 mL, 0.47 mmol). The mixture was allowed to warm up to room temperature and stirred for 30 minutes. The resultant mixture was quenched with Na2CO3 (aq). The cloudy suspension was filtered and washed with water. The filtrate was extracted with ethyl acetate and the organic layer was washed with brine and evaporated. Purification by preparative LCMS (pH 10) gave the desired compound (2.8 mg, 11%). LCMS calculated for C18H20ClN8O (M+H)+: m/z=399.1. found: 398.9.

Workup

  1. customThe resultant mixture was quenched with Na2CO3 (aq)
  2. filtrationThe cloudy suspension was filtered
  3. washwashed with water
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. customevaporated
  7. customPurification by preparative LCMS (pH 10)

Sources & evidence

ORD record
ord-864d70838b2d4436804081c0b9c39bb2
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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