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

HRID 710150노트

반응식

HRID 710150 반응식
[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]

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 71089562Methyl 6-{2-(1-(isopropoxycarbonyl)piperidin-4-yl)-benzo[d]oxazol-5-yl]nicotinate2회HCID 71090092Isopropyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-yl)piperidine-1-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-31ed7333a4214d0783c5d8aaadd36429
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181214B2

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