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

HRID 1641291ノート

反応式

HRID 1641291 の反応式
[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]

参加物

6

反応物 4

HCID 887MethanolHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 59553169HCID 59553169、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7a7d23be24924ca6a1eb5ecd3f7f5227
出典データセット
uspto-grants-2012_02
特許番号
US08114873B2

反応ノート

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