2-Methylpropyl 2-(2-methylpropoxy)-1(2H)-quinolinecarboxylate → HCID 54453861, compound

HRID 434623Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:10]([NH:12][C@@H:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([OH:16])=O)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[NH2:24][CH2:25][CH2:26][NH:27][CH2:28][CH:29]([OH:42])[CH2:30][O:31][C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1.C(OC1C=CC2C(=CC=CC=2)N1C(OCC(C)C)=O)C(C)C.C(=O)(O)[O-].[Na+]>CS(C)=O>[NH2:1][C:2]1[C:3]([C:10]([NH:12][CH:13]([C:14](=[O:16])[NH:24][CH2:25][CH2:26][NH:27][CH2:28][CH:29]([OH:42])[CH2:30][O:31][C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[CH:34][CH:33]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A stirred mixture of (S)-2-(3,5-diamino-6-chloropyrazine-2-carboxamido)-3-phenylpropionic acid (1.8 g.), 1-β-aminoethylamino-3-α-naphthyloxypropan-2-ol (1.43 g.), 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline (1.5 g.) and dimethylsulphoxide (30 ml.) was heated at 75° C. for 18 hours, cooled and poured into ice-water (600 ml.). Aqueous 6% w/v sodium bicarbonate solution (50 ml.) was added, the mixture was filtered and the solid product was washed with diethylether (100 ml.). There was thus obtained as solid product 3,5-diamino-6-chloro-N-{1-[N-β-(2-hydroxy-3-α-naphthyloxypropylamino)ethylcarbamoyl]-2-phenylethyl}pyrazine-2-carboxamide, m.p. 142°-146° C.

Workup

temperaturecooled
additionwas added
filtrationthe mixture was filtered
washthe solid product was washed with diethylether (100 ml.)

Sources & evidence

ORD record: ord-6f6e74213cc742aea2aa32eddc71bd55
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04399138

Reaction notes

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