Triethylamine → HCID 71237441, compound

HRID 1045791Notes

Reaction equation

HRID 1045791 reaction equation
[NH2:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]2[CH:13]=[CH:14][CH:15]=[N:16][C:5]=2[N:4]([CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:3]1=[O:27].C(N(CC)CC)C.ON1C2=NC=CC=C2N=N1.[C:45]([O:49][C:50]([NH:52][C@@H:53]([CH3:57])[C:54](O)=[O:55])=[O:51])([CH3:48])([CH3:47])[CH3:46].Cl.CN(C)CCCN=C=NCC>ClCCl>[Si:20]([O:19][CH2:18][CH2:17][N:4]1[C:5]2[N:16]=[CH:15][CH:14]=[CH:13][C:6]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:2]([NH:1][C:54](=[O:55])[C@@H:53]([NH:52][C:50](=[O:51])[O:49][C:45]([CH3:47])([CH3:46])[CH3:48])[CH3:57])[C:3]1=[O:27])([C:23]([CH3:24])([CH3:26])[CH3:25])([CH3:21])[CH3:22]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71237051HCID 71237051, compound

Product 1

HCID 71237441HCID 71237441, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cool a mixture of 7-amino-5-[2-(tert-butyl(dimethyl)silyl)oxyethyl]-7H-pyrido[2,3-d][3]benzazepin-6-one (36.3 g, 89.9 mmol), dichloromethane (360 mL), triethylamine (16.3 mL, 116.9 mmol), 3-hydroxytriazolo[4,5-b]pyridine (15.9 g, 116.9 mmol), and (2S)-2-(tert-butoxycarbonylamino)propanoic acid (22.5 g, 116.9 mmol) to 0° C. Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (22.4 g, 116.9 mmol) and after 5 minutes allow to warm to ambient temperature overnight. Wash with water (500 mL×2), saturated aqueous sodium bicarbonate solution (2×300 mL), brine (300 mL), and then dry over sodium sulfate and concentrate. Purify the residue by flash chromatography, eluting with isopropyl alcohol:hexane (5:95 to 10:90) to give the title compound as a white foam (43.14 g, 77.77 mmol, 86.50%). MS (m/z): 555 (M+1).

Workup

  1. temperatureCool
  2. washWash with water (500 mL×2), saturated aqueous sodium bicarbonate solution (2×300 mL), brine (300 mL)
  3. dry with materialdry over sodium sulfate
  4. concentrationconcentrate
  5. customPurify the residue by flash chromatography
  6. washeluting with isopropyl alcohol:hexane (5:95 to 10:90)

Sources & evidence

ORD record
ord-c4698a712e314ca6b7c8c6dc02a1bc95
Source dataset
uspto-grants-2013_10
Patent number
US08569286B2

Reaction notes

Loading…