Potassium Carbonate → 6-{2-[1-(Isopropoxycarbonyl)piperidin-4-yl]benzo[d]oxazol-5-yl}nicotinic acid

HRID 710150ノート

反応式

HRID 710150 の反応式
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([C:22]4[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][N:23]=4)=[CH:18][C:16]=3[N:17]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB(C2C=CC3OC(C4CCN(C(OC(C)C)=O)CC4)=NC=3C=2)O1.ClC1C=CC(C(OC)=O)=CN=1.C([O-])([O-])=O.[K+].[K+]>CO>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([C:22]4[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[CH:24][N:23]=4)=[CH:18][C:16]=3[N:17]=2)[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 71089562Methyl 6-{2-(1-(isopropoxycarbonyl)piperidin-4-yl)-benzo[d]oxazol-5-yl]nicotinate2 回HCID 71090092Isopropyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-yl)piperidine-1-carboxylate

生成物 1

HCID 711142036-{2-[1-(Isopropoxycarbonyl)piperidin-4-yl]benzo[d]oxazol-5-yl}nicotinic acid収率 41.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Following the General Procedure-2, Methyl 6-{2-(1-(isopropoxycarbonyl)piperidin-4-yl)-benzo[d]oxazol-5-yl]nicotinate (50 mg) was prepared from Intermediate 14 (400 mg, 0.97 mmol) and methyl 6-chloronicotinate (166 mg, 0.97 mmol) as a brown solid. Methyl 6-{2-(1-(isopropoxycarbonyl)piperidin-4-yl)-benzo[d]oxazol-5-yl]nicotinate (35 mg, 0.08 mmol) was dissolved in MeOH (5 ml) and added K2CO3 (22 mg, 0.17 mmol). This mixture was stirred at reflux for overnight. MeOH removed on rotavapour and pH adjusted to 6 using acetic acid to obtain a solid. Solid was filtered and dried to obtain the titled compound (20 mg) as a grey solid. M. P.: 239-242° C. MS (m/z): 410.4 [M+H]+.

後処理

  1. temperatureat reflux for overnight
  2. customMeOH removed on rotavapour
  3. customto obtain a solid
  4. filtrationSolid was filtered
  5. customdried

出典と根拠

ORDレコード
ord-31ed7333a4214d0783c5d8aaadd36429
出典データセット
uspto-grants-2015_11
特許番号
US09181214B2

反応ノート

読み込み中…