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

HRID 710150Notes

Reaction equation

HRID 710150 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-31ed7333a4214d0783c5d8aaadd36429
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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