Diisopropylethylamine → N~2~-1,3-Benzoxazol-2-YL-3-cyclohexyl-N-{2-[(4-methoxyphenyl)amino]ethyl}-L-alaninamide

HRID 969786Notes

Reaction equation

HRID 969786 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@@H:11]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:12]([OH:14])=O.Cl.Cl.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][CH2:33][CH2:34][NH2:35])=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@@H:11]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:12]([NH:35][CH2:34][CH2:33][NH:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=1)=[O:14]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 210822522-(S)-(benzooxazol-2-ylamino)-3-cyclohexyl propionic acidHCID 21082260n1-(4-Methoxy-phenyl)-ethane-1,2-diamine-2hcl

Product 1

HCID 6420159N~2~-1,3-Benzoxazol-2-YL-3-cyclohexyl-N-{2-[(4-methoxyphenyl)amino]ethyl}-L-alaninamideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-(S)-(benzooxazol-2-ylamino)-3-cyclohexyl propionic acid (288 mg, 1.0 mmol), N1-(4-methoxy-phenyl)-ethane-1,2-diamine-2HCl (239 mg, 1.0 mmol), and iPr2NEt (0.87 mL, 5.0 mmol) in dichloromethane (4 mL) was added HATU (418 mg, 1.1 mmol). The solution was stirred at room temperature for 4 hours and then evaporated to dryness. The crude material was chromatographed over silica gel (Hexanes/EtOAc) to afford the title compound as a white powder (243 mg, 56%). HPLC-MS calcd. for C25H32N4O3 (M+H+) 437.25, found 437.5.

Workup

  1. customevaporated to dryness
  2. customThe crude material was chromatographed over silica gel (Hexanes/EtOAc)

Sources & evidence

ORD record
ord-44a3445fdd414ccfaa724d69e1e6ff6e
Source dataset
uspto-grants-2007_12
Patent number
US07307095B2

Reaction notes

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