Triethylamine → HCID 69285658, compound

HRID 2225236Notes

Reaction equation

HRID 2225236 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]1[CH2:11][CH2:10][C@@H:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][C@H:7]1[CH2:17][CH2:18][CH2:19][CH3:20])=[O:4].[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](O)=[O:27].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:17]([C@@H:7]1[CH2:8][C@H:9]([NH:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:10][CH2:11][C@@H:6]1[NH:5][C:3](=[O:4])[CH2:2][NH:1][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][CH:31]=[C:23]([C:22]([F:21])([F:32])[F:33])[CH:24]=1)[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 99633-(Trifluoromethyl)benzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69285591HCID 69285591, compound

Product 1

HCID 69285658HCID 69285658, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A sample of 2-amino-N-((1S,2R,4R)-2-butyl-4-(tert-butylamino)cyclohexyl)acetamide was combined with 3-Trifluoromethylbenzoic acid (1 equivalent), EDCI (1 equivalent), HOBT (1.1 equivalents), and triethylamine (1 equivalent) in 2 mL of CH2Cl2 was stirred at room temperature overnight. The reaction mixture was directly chromatographed on silica gel (eluting with 2-8% NH4OH/MeOH/CH2Cl2) to give N-(2-((1S,2R,4R)-2-butyl-4-(tert-butylamino)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide as a white solid. MS found: (M+H)+=456.47; 1H NMR (400 MHz, CDCl3) δ(TMS): 0.83-1.98 (m, 25H), 2.67-2.79 (m, 1H) 4.12-4.28 (m, 3H), 6.80-6.90 (m, 1H), 7.49-7.63 (m, 2H), 7.78-7.84 (m, 1H), 8.00-8.06 (m, 1H), 8.15 (s, 1H).

Workup

  1. customThe reaction mixture was directly chromatographed on silica gel (eluting with 2-8% NH4OH/MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6818855ffc6d40c18fef29b4074059e3
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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