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

HRID 1394218노트

반응식

HRID 1394218 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-bf588f2e3b4b4f30bded9fc398708daf
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348339B2

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