Acetic Acid → HCID 118135076, 화합물

HRID 926118노트

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HRID 926118 반응식
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH:18]=O)=[CH:17][C:12]=3[C:11]3=[N:20][CH:21]=[N:22][N:10]3[C:9]2=[O:23])=[CH:5][CH:4]=1.[CH:26]12[CH2:32][CH:29]([NH:30][CH2:31]1)[CH2:28][O:27]2.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(#N)C>[CH:26]12[CH2:32][CH:29]([N:30]([CH2:18][C:16]3[CH:15]=[N:14][C:13]4[N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:25][CH:24]=5)[C:9](=[O:23])[N:10]5[N:22]=[CH:21][N:20]=[C:11]5[C:12]=4[CH:17]=3)[CH2:31]1)[CH2:28][O:27]2

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 36145512-Oxa-5-azabicyclo(2.2.1)heptaneHCID 5003444Sodium cyanoborohydrideHCID 867053916-(4-Methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-9-carbaldehyde

생성물 1

HCID 118135076HCID 118135076, 화합물수율 55.8%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

실험 절차

6-(4-Methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-9-carbaldehyde (49 mg, 0.15 mmol), 2-oxa-5-azabicyclo[2.2.1]heptane (49 mg, 0.36 mmol), ACN (1 mL), TEA (0.051 mL, 0.37 mmol) and acetic acid (0.040 mL, 0.69 mmol) were combined and stirred for 10 minutes. Sodium cyanoborohydride (18 mg, 0.29 mmol) was added and the mixture was stirred for 18 h at room temperature. The mixture was diluted with methanol, filtered, and purified by preparative HPLC to afford the title compound (35 mg, 45%) as the trifluoroacetic acid salt as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.25 (d, J=11.42 Hz, 1H), 2.43 (br s, 1H), 3.44-3.63 (m, 2H), 3.76 (s, 3H), 3.91 (d, J=10.42 Hz, 1H), 4.37-4.53 (m, 3H), 4.56-4.65 (m, 1H), 4.73 (s, 1H), 5.74 (s, 2H), 6.76-6.91 (m, 2H), 7.60 (d, J=8.78 Hz, 2H), 8.38 (s, 1H), 8.83 (s, 1H), 9.08 (s, 1H). [M+H]=419.2.

후처리

  1. stirringthe mixture was stirred for 18 h at room temperature
  2. filtrationfiltered
  3. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-92a09c8abf2a4824b98483fc8db161ab
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284335B2

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