Triethylamine → HCID 24986042, 화합물

HRID 388144

반응식

HRID 388144 반응식
O[CH2:2][C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]4[N:20]([CH2:24][CH2:25][CH:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)[C:21](=[O:23])[NH:22][C:17]4=[N:16][CH:15]=3)=[CH:10][CH:9]=2)[N:4]=1.O=C1NC2=NC=C(C3C=CC(C(=N)OCC)=CC=3)N=C2[N:34]1CCC1CCOCC1.OCC(NN)=O.C(N(CC)CC)C>C(O)C>[NH2:34][CH2:2][C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]4[N:20]([CH2:24][CH2:25][CH:26]5[CH2:27][CH2:28][O:29][CH2:30][CH2:31]5)[C:21](=[O:23])[NH:22][C:17]4=[N:16][CH:15]=3)=[CH:10][CH:9]=2)[N:4]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 3505362-HydroxyacetohydrazideHCID 66699925HCID 66699925, 화합물HCID 666999366-(4-(5-(Hydroxymethyl)-1H-1,2,4-triazol-3-yl)phenyl)-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one

생성물 1

HCID 24986042HCID 24986042, 화합물수율 49%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
110 °C

실험 절차

6-(4-(5-(Hydroxymethyl)-1H-1,2,4-triazol-3-yl)phenyl)-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. Ethyl 4-(2-oxo-3-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)benzimidate (See Example 195.B) (0.250 g, 0.63 mmol) in ethanol (20 mL) was treated with 2-hydroxyacetohydrazide (0.17 g, 1.9 mmol) and triethylamine (0.26 mL, 1.9 mmol), and the resulting reaction mixture was stirred in a sealed tube at 110° C. for 16 h. The cooled reaction solvent removed under reduced pressure. The resulting material was purified using reverse-phase semi-preparatory HPLC (15-50% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). Fractions containing clean product were passed through a Phenomenex Strata-X-C ion exchange column to remove TFA. The column was washed successively with water, methanol, and then 5% ammonium hydroxide in methanol. The product came off with the 5% ammonium hydroxide in methanol eluent and was concentrated on a rotary evaporator. The residue was triturated with ethyl ether in hexane to make a fine powder and dried under vacuum at 50° C. to give the desired product (0.130 g, 49%) as a white solid. MS (ESI) m/z 422.3[M+1]+.

후처리

  1. customthe resulting reaction mixture
  2. customThe cooled reaction solvent
  3. customremoved under reduced pressure
  4. customThe resulting material was purified
  5. customreverse-phase semi-preparatory HPLC (15-50% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)
  6. additionFractions containing clean product
  7. customto remove TFA
  8. washThe column was washed successively with water, methanol
  9. concentrationwas concentrated on a rotary evaporator
  10. customThe residue was triturated with ethyl ether in hexane
  11. customdried under vacuum at 50° C.

출처 및 근거

ORD 기록
ord-0288cb365c044e178462c2ebe0bfc778
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372976B2

연결된 노트

불러오는 중…