2-Pyrazinecarboxylic acid → HCID 22256455, compound

HRID 351182Notes

Reaction equation

HRID 351182 reaction equation
C(OC([N:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:12][CH:11]=1)=O)(C)(C)C.[N:35]1[CH:40]=[CH:39][N:38]=[CH:37][C:36]=1[C:41]([OH:43])=O.C(N(CC)C(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]([CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)[C:41]([C:36]2[CH:37]=[N:38][CH:39]=[CH:40][N:35]=2)=[O:43])=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22018600N-(t-butoxycarbonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 22256455HCID 22256455, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(t-butyloxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (183 mg, 0.40 mmol) in dry CH2Cl2 (5 mL) was added 2-pyrazinecarboxylic acid (68 mg, 0.55 mmol), N,N -diisopropylethylamine (0.21 mL, 1.21 mmol), 1-hydroxybenzotriazole hydrate (81 mg, 0.60 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl (EDC) (115 mg, 0.60 mmol) and the mixture was stirred at room temperature for 20 hours. Following standard work-up procedures, the crude material was purified by column chromatography on silica gel (CH2Cl2/MeOH, 98:2 followed by 95:5) to give the desired amide (131 mg, 58%) as a colorless oil.

Workup

  1. customthe crude material was purified by column chromatography on silica gel (CH2Cl2/MeOH, 98:2 followed by 95:5)

Sources & evidence

ORD record
ord-711f739862a448beb9e0ed6e0a5adf1b
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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