Trimethyl borate → 1H-Imidazo[4,5-c]pyridin-7-ol, 2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-

HRID 1394218ノート

反応式

HRID 1394218 の反応式
Br[C:2]1[C:3]2[N:10]([CH2:11][CH3:12])[C:9]([C:13]3[C:14]([NH2:18])=[N:15][O:16][N:17]=3)=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1.C([Li])CCC.C[O:25]B(OC)OC>O1CCCC1>[NH2:18][C:14]1[C:13]([C:9]2[N:10]([CH2:11][CH3:12])[C:3]3[C:2]([OH:25])=[CH:7][N:6]=[CH:5][C:4]=3[N:8]=2)=[N:17][O:16][N:15]=1

参加物

5

反応物 3

HCID 8470Trimethyl borateHCID 443971924-(7-Bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amineHCID 178418339Butyllithium

生成物 1

HCID 596818031H-Imidazo[4,5-c]pyridin-7-ol, 2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-収率 58%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of the product from Example 100 (2.6 g, 8.41 mmol) in tetrahydrofuran (180 ml) at −78° C. was treated with a 2.5M solution of n-butyllithium (8.41 ml, 21.03 mmol) in hexanes. After the addition was complete the mixture was treated with trimethylborate (2.62 g, 25.23 mmol) and allowed to reach room temperature. After 1.5 hours at room temperature the reaction was carefully quenched with 3M aq. NaOH (12.5 ml) followed by a 30% aqueous hydrogen peroxide solution (4.3 ml). After 45 minutes the reaction was acidified with 2M hydrochloric acid and then applied to a SCX ion exchange column and eluted with methanol and then a mixture of methanol/0.880 ammonia (9:1). The basic fractions were then reduced and the solid residue was triturated with dichloromethane and filtered to afford the title compound, (1.2 g, 58%); MS (ES+) m/e 247 [M+H]+.

後処理

  1. additionAfter the addition
  2. customto reach room temperature
  3. customAfter 1.5 hours at room temperature the reaction was carefully quenched with 3M aq. NaOH (12.5 ml)
  4. washeluted with methanol
  5. additiona mixture of methanol/0.880 ammonia (9:1)
  6. customthe solid residue was triturated with dichloromethane
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-bf588f2e3b4b4f30bded9fc398708daf
出典データセット
uspto-grants-2008_03
特許番号
US07348339B2

反応ノート

読み込み中…