HCID 275791, compound → HCID 69203895, compound

HRID 2114138Notes

Reaction equation

HRID 2114138 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:28]2[CH:37]=[C:36]([C:38](O)=[O:39])[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([CH3:41])[CH:34]=3)[N:29]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1>[CH:22]1([C:28]2[CH:37]=[C:36]([C:38]([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:39])[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([CH3:41])[CH:34]=3)[N:29]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 275791HCID 275791, compoundHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

Product 1

HCID 69203895HCID 69203895, 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-cyclohexyl-6-methylquinoline-4-carboxylic acid (107.7 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-cyclohexyl-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-6-methylquinoline-4-carboxamide. NMR; δH [2H6]—DMSO 10.69,(1H, s), 8.62,(1H, t), 7.95-7.90,(3H, m), 7.82,(1H, s), 7.70,(2H, m), 7.60,(1H, dd, 7.56, (1H, s), 7.46,(2H, d), 7.33,(1H, d), 3.16,(2H, t), 2.90,(1H, m), 2.47,(3H, s), 2.22,(3H, s), 1.95,(2H, m), 1.84,(2H, m), 1.74-1.61,(3H, m), .46-1.26,(3H, m), 1.04,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.93 min, MH+532.

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-a6fb3c530cda4933964fda63d6762a74
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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