Ethanol → HCID 11635877, compound

HRID 2378119Notes

Reaction equation

HRID 2378119 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:48])([F:47])[C:10]1[CH:11]=[C:12]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)[CH2:13][N:14]([C:34]1[N:35]=[N:36][N:37]([CH3:39])[N:38]=1)[C@@H:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[N:23]=2)[N:18]([C:29](Cl)=[O:30])[C@H:17]([CH2:32][CH3:33])[CH2:16]1.[CH2:49]([OH:51])[CH3:50]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:49]([O:51][C:29]([N:18]1[C:19]2[C:24](=[N:23][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:21][CH:20]=2)[C@@H:15]([N:14]([CH2:13][C:12]2[CH:40]=[C:41]([C:43]([F:44])([F:45])[F:46])[CH:42]=[C:10]([C:9]([F:48])([F:47])[F:8])[CH:11]=2)[C:34]2[N:35]=[N:36][N:37]([CH3:39])[N:38]=2)[CH2:16][C@H:17]1[CH2:32][CH3:33])=[O:30])[CH3:50]

Participants

6

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 58926748HCID 58926748, compound

Product 1

HCID 11635877HCID 11635877, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Add triethylamine (25 μL) and 4-dimethylaminopyridine (10 mg, 80 μmol) to a solution of (2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carbonyl chloride (100 mg, 0.16 mmol) and ethanol (28 μL) in dichloromethane (0.9 mL). Stir the mixture at room temperature for 8 h. Evaporate the solvent and purify the crude material by silica gel chromatography (elution with hexane/ethyl acetate) to afford the title compound (51 mg, 51%). MS (ES+): 626 (M+H).

Workup

  1. customEvaporate the solvent
  2. custompurify the crude material
  3. washby silica gel chromatography (elution with hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0116a7f7a862459680a1dd687a314052
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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