Methanol → 3-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamide

HRID 1641291노트

반응식

HRID 1641291 반응식
[C:1]([CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([NH:15][C:16](=[O:31])[C:17]2[CH:22]=[C:21]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[CH:20]=[C:19]([F:30])[CH:18]=2)=[CH:7][CH:6]=1)#[N:2].C[Si]([N:36]=[N+:37]=[N-:38])(C)C.C([Sn](=O)CCCC)CCC.CO>C1(C)C=CC=CC=1>[F:30][C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([N:23]2[CH2:24][CH2:25][CH:26]([CH3:29])[CH2:27][CH2:28]2)[CH:20]=1)[C:16]([NH:15][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([O:4][CH2:3][C:1]2[N:36]=[N:37][NH:38][N:2]=2)=[CH:6][CH:7]=1)=[O:31]

참가 물질

6

반응물 4

HCID 887MethanolHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 59553169HCID 59553169, 화합물

생성물 1

HCID 595530853-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamide수율 0%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

N-(4-Cyanomethoxynaphthalen-1-yl)-3-fluoro-5-(4-methylpiperidin-1-yl)-benzamide (54 mg, 129 mmol), trimethylsilylazide (0.1 ml, 760 mmol) and dibutyltin oxide (5 mg) are heated to reflux in anhydrous toluene (3 ml) for 5 hours. After cooling to room temperature methanol (5 ml) is then added and the mixture stirred at room temperature for 30 min. The mixture is then evaporated to dryness and the residue recrystalized from ethyl acetate/hexanes to give 3-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamide as a grey powder (22 mg). 1H NMR 300 MHz (DMSO-d6) 10.3(s, 1H), 8.32(dd, 1H, J=8.7 and 2.7 Hz), 7.87(d, 1H, J=9.3 Hz), 7.54-7.62(m, 2H), 7.42-7.5(m, 2H), 7.17(dd, 1H, J=15.9 and 9.3 Hz), 6.97(d, 1H, J=13.2 Hz), 5.7(s, 2H), 3.85(d, 2H, J=19.8 Hz), 2.77(m, 2H), 1.5-1.78(m, 3H), 1.25(m, 2H), 0.95(d, 3H, J=6.6 Hz).

후처리

  1. additionis then added
  2. customThe mixture is then evaporated to dryness
  3. customthe residue recrystalized from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-7a7d23be24924ca6a1eb5ecd3f7f5227
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114873B2

반응 노트

불러오는 중…