Diisopropylethylamine → HCID 11670360, compound

HRID 553180Notes

Reaction equation

HRID 553180 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[CH2:8][CH:7]([NH:13][CH:14]([CH2:18][CH2:19][CH3:20])[C:15]([OH:17])=O)[CH2:6][CH2:5]2.[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.C(N(C(C)C)CC)(C)C.[CH3:50][C:51]([CH3:65])([CH3:64])[CH2:52][NH:53][CH2:54][C:55]([N:58]1[CH:62]=[C:61]([NH2:63])[N:60]=[CH:59]1)([CH3:57])[CH3:56]>CN(C=O)C.C(Cl)Cl>[CH3:50][C:51]([CH3:65])([CH3:64])[CH2:52][NH:53][CH2:54][C:55]([N:58]1[CH:62]=[C:61]([NH:63][C:15](=[O:17])[CH:14]([NH:13][CH:7]2[CH2:6][CH2:5][C:4]3[C:9](=[C:10]([F:12])[CH:11]=[C:2]([F:1])[CH:3]=3)[CH2:8]2)[CH2:18][CH2:19][CH3:20])[N:60]=[CH:59]1)([CH3:56])[CH3:57]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 211128022-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acidHCID 67163806HCID 67163806, compound

Product 1

HCID 11670360HCID 11670360, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Combine 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid (1 equiv) derived from diasteromer #2 above, TPTU (1 equiv), diisopropylethylamine (2 equiv) in DMF followed by 1-[2-(2,2-dimethyl-propylamino)-1,1-dimethyl-ethyl]-1H-imidazol-4-ylamine (2 equiv) in methylene chloride. The reaction is stirred overnight at rt, quenched with aq. sodium bicarbonate, and extracted with methylene chloride. The solvent is dried, concentrated, and purified by silica gel chromatography to afford diastereomer #2 of the title compound: C13 NMR (100 MHz, CDCl3) 14.1, 19.5, 26.4, 27.8, 28.2, 28.9, 29.8, 32.1, 36.6, 38.8, 52.8, 59.1, 60.9, 61.3, 63.0, 100.8, 101.0, 101.3, 104.5, 110.6, 110.8, 110.9, 131.2, 137.6, 139.8, 159.8, 172.4; MS m/z 490.2 (M+1).

Workup

  1. customquenched with aq. sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. customThe solvent is dried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-9e75e5bfb17d451c98dcfd84490a904f
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

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