2-cyclopropylquinoline-4-carboxylic acid → HCID 69203211, compound

HRID 2114139Notes

Reaction equation

HRID 2114139 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[CH:22]1([C:25]2[CH:34]=[C:33]([C:35](O)=[O:36])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=2)[CH2:24][CH2:23]1>C1COCC1>[CH:22]1([C:25]2[CH:34]=[C:33]([C:35]([NH:1][C:2]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]5[CH2:20][CH2:19]5)=[O:15])=[CH:10][CH:9]=4)[C:5]([CH3:21])=[CH:4][CH:3]=3)=[O:36])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 2757852-cyclopropylquinoline-4-carboxylic acidHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

Product 1

HCID 69203211HCID 69203211, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (42 mg, 0.15 mmol) and 2-cyclopropylquinoline-4-carboxylic acid (85.3 mg, 0.4 mmol) were mixed in THF (5 ml) and the mixture shaken in a varian tube for 30 min at room temperature. Carbodiimde resin (442 mg, 0.5 mmol) was added and shaking continued for 18 h. The solution was filtered off, the resin washed with THF and methanol and the combined filtrate and washings reduced to dryness under vacuum. The residue was dissolved in ethyl acetate, washed with hydrochloric acid (1M) and aqueous sodium hydrogen carbonate. The solvent was evaporated from the organic fraction under vacuum to give 2-cyclopropyl-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)quinoline-4-carboxamide. NMR; δH [2H6]—DMSO 10.74,(1H, s), 8.62,(1H, t), 8.04,(1H, d), 7.94-7.90,(3H, m), 7.74-7.70,(3H, m), 7.62,(1H, s), 7.53,(1H, m), 7.45,(2H, d), 7.33,(1H, d), 3.16,(2H, t), 2.37,(1H, m), 2.22,(3H, s), 1.15-1.10,(5H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.61 min, MH+476.

Workup

  1. stirringshaking
  2. waitcontinued for 18 h
  3. filtrationThe solution was filtered off
  4. washthe resin washed with THF and methanol
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with hydrochloric acid (1M) and aqueous sodium hydrogen carbonate
  7. customThe solvent was evaporated from the organic fraction under vacuum

Sources & evidence

ORD record
ord-acb732e531f64193a31cce529605ccf9
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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