Diisopropylethylamine → HCID 54440666, compound

HRID 1069451Notes

Reaction equation

HRID 1069451 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[N:39]1([C:46]([NH:48][C@@H:49]([CH2:53][CH:54]([CH3:56])[CH3:55])[C:50](O)=[O:51])=[O:47])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH:19]2[CH2:24][CH2:23][N:22]([C:50](=[O:51])[C@@H:49]([NH:48][C:46]([N:39]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)=[O:47])[CH2:53][CH:54]([CH3:56])[CH3:55])[CH2:21][CH2:20]2)[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:14][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acidHCID 18380603HCID 18380603, compound

Product 1

HCID 54440666HCID 54440666, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Benzyloxycarbonylamino-phenyl)-(3-methyl-butyl)-piperidin-4yl-amine (0.22 g, 5.64 mmol) was dissolved in DMF (30 mL), treated with Hunig's base (3.93 mL, 22.6 mmol), (S)-2-[(Azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid (1.36 g, 5.64 mmol), and HBTU (2.04 g, 5.64 mmol), and stirred for 1 hour. The reaction was diluted with EtOAc (200 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 5% MeOH/CH2Cl2 to give 2.76 g (77%) of the desired product.

Workup

  1. washwashed with saturated bicarbonate solution and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel eluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-6926bc13f7d0408b93eef93b0e106df2
Source dataset
uspto-grants-2001_06
Patent number
US06251918B1

Reaction notes

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