2-Pyrazinecarboxylic acid → HCID 178521777, compound

HRID 2047568Notes

Reaction equation

HRID 2047568 reaction equation
[N:1]1([C@@H:7]2[CH2:10][C@H:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[C:27](O)=[O:28].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[OH-].[Na+]>ClCCl.O>[N:1]1([C@@H:7]2[CH2:10][C@H:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([NH:20][C:27]([C:22]5[CH:23]=[N:24][CH:25]=[CH:26][N:21]=5)=[O:28])[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178507336HCID 178507336, compound

Product 1

HCID 178521777HCID 178521777, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The product of Example 101A (59 mg, 0.206 mmole) was dissolved in anhydrous dichloromethane (2.0 mL). To the solution was added 2-pyrazine carboxylic acid (51 mg, 0.412 mmole), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (79 mg, 0.412 mmole) and 1-hydroxybenzotriazole hydrate (28 mg, 0.206 mmole). The mixture was stirred at room temperature overnight then diluted with water. The pH of the mixture was was adjusted to pH 9 with 1N NaOH and extracted three times with dichloromethane. The combined organic layers were concentrated to give the crude product. The crude product was purified by column chromatography (0.6% ammonium hydroxide and 6% methanol in dichloromethane) to provide the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 9.81 (s, 1H) 9.54 (d, J=1.53 Hz, 1H) 8.83 (d, J=2.44 Hz, 1H) 8.66 (d, J=2.14 Hz, 1H) 8.58-8.63 (m, 1H) 7.94 (d, J=8.85 Hz, 1H) 7.52 (dd, J=8.85, 2.14 Hz, 1H) 3.52-3.62 (m, 1H) 2.74-2.84 (m, 1H) 2.61-2.72 (m, 2H) 2.24-2.41 (m, 6H) 1.55-1.64 (m, 4H) 1.40-1.52 (m, 2H). MS: (M+H)+=394.

Workup

  1. extractionextracted three times with dichloromethane
  2. concentrationThe combined organic layers were concentrated
  3. customto give the crude product
  4. customThe crude product was purified by column chromatography (0.6% ammonium hydroxide and 6% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3a39c9bf8d814236982ecc639dae3e2c
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

Loading…