Diisopropylethylamine → HCID 68412017, compound

HRID 1993500Notes

Reaction equation

HRID 1993500 reaction equation
[NH2:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([NH:12][C:13](=[O:22])[C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)([CH2:5]3)[CH2:3]1)[CH2:9]2.[Cl:23][CH2:24][C:25]([N:27]1[CH2:31][C:30]([F:33])([F:32])[CH2:29][C@H:28]1[C:34]#[N:35])=[O:26].CCN(C(C)C)C(C)C>C(#N)C>[OH2:20].[ClH:23].[ClH:23].[C:34]([C@@H:28]1[CH2:29][C:30]([F:32])([F:33])[CH2:31][N:27]1[C:25](=[O:26])[CH2:24][NH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([NH:12][C:13](=[O:22])[C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)([CH2:5]3)[CH2:3]1)[CH2:9]2)#[N:35]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 45081037(2S)-1-(Chloroacetyl)-4,4-difluoropyrrolidine-2-carbonitrileHCID 67480765HCID 67480765, compound

Product 1

HCID 68412017HCID 68412017, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

132 mg (0.45 mmole) of N-(3-Amino-1-adamantyl)-4-methoxybenzamide are reacted with 87 mg (0.42 mmole) of (2S)-1-(chloroacetyl)-4,4-difluoro-pyrrolidine-2-carbonitrile in the presence 340 mg (1.32 mmole) PS-DIEA in 25 ml acetonitrile, as described in Example 2/b.). After work-up and chromatographic purification (chloroform-methanol-25% aqueous ammonia solution 9:1:0.1) and acidification ethereal hydrochloride acide the title compound is obtained: 90 mg (46%). M.p.: 160-161° C. 1H-NMR (DMSO-d6): 1.60 (dd, 2H), 1.85 (m, 6H), 2.14 (m, 2H), 2.30 (m, 2H), 2.38 (m, 2H), 2.87 (m, 2H), 3.79 (s, 3H), 4.17 (m, 2H), 4.26 (m, 1H), 4.47 (m, 1H), 5.21 (m, 1H), 6.95 (d, 2H), 7.71 (s, 1H), 7.77 (d, 2H), 9.41 (b, 2H), 9.02 (b, 2H).

Workup

  1. customAfter work-up and chromatographic purification (chloroform-methanol-25% aqueous ammonia solution 9:1:0.1) and acidification ethereal hydrochloride
  2. customis obtained

Sources & evidence

ORD record
ord-ff5cb9b1fdf8453cb275377a284e1bf4
Source dataset
uspto-grants-2010_01
Patent number
US07652021B2

Reaction notes

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