Dichloromethane → HCID 178463544, compound

HRID 717850Notes

Reaction equation

HRID 717850 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.C(Cl)Cl.B(Br)(Br)Br>>[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 3

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 178496658HCID 178496658, compound

Product 1

HCID 178463544HCID 178463544, compoundYield 12%

Procedure

To a cooled solution of N-(1-{8-chloro-5-[(3S)-3-methoxypyrrolidin-1-yl]imidazo[1,5-a]pyridin-6-yl}ethyl)-9H-purin-6-amine (18.0 mg, 0.0436 mmol) in methylene chloride (1.0 mL, 16 mmol) 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 (2.0 mg, 12%). LCMS calculated for C18H20ClN8O (M+H)+: m/z=399.1. found: 399.0.

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-aec779b6dad1423c8712adfbb433a463
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

Loading…