Diisopropylethylamine → HCID 54151454, compound

HRID 2299895Notes

Reaction equation

HRID 2299895 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:25][CH:26]=[C: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>CCOC(C)=O.CN(C=O)C>[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][CH:26]=[C: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 18380800HCID 18380800, compound

Product 1

HCID 54151454HCID 54151454, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Benzyloxycarbonylamino-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amine (0.35 g, 0.88 mmol) was dissolved in; DMF (8 mL), treated with Hunig's base (0.47 mL, 2.64 mmol), (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid (0.21 g, 0.88 mmol), and HBTU (0.34 g, 0.88 mmol). The reaction was stirred 2 hours, then diluted with EtOAc (100 mL), washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 5% MeOH/CH2Cl2 to give 0.49 g (93%) of the desired product.

Workup

  1. washwashed with saturated sodium 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-334a406473444102a16df1c50c2247a2
Source dataset
uspto-grants-2002_12
Patent number
US06495715B2

Reaction notes

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