2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → HCID 68415424, compound

HRID 1993499Notes

Reaction equation

HRID 1993499 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][NH:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][C:11]([NH2:19])([CH2:12]3)[CH2:10]1)[CH2:16]2)([O-:3])=[O: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].C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C>C(#N)C>[ClH:23].[ClH:23].[ClH:23].[F:33][C:30]1([F:32])[CH2:31][N:27]([C:25](=[O:26])[CH2:24][NH:19][C:11]23[CH2:12][CH:13]4[CH2:14][CH:15]([CH2:16][C:9]([NH:8][CH2:7][C:6]5[CH:20]=[CH:21][CH:22]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=5)([CH2:18]4)[CH2:10]2)[CH2:17]3)[C@H:28]([C:34]#[N:35])[CH2:29]1

Participants

5

Reactant 3

HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 45081037(2S)-1-(Chloroacetyl)-4,4-difluoropyrrolidine-2-carbonitrileHCID 68412925HCID 68412925, compound

Product 1

HCID 68415424HCID 68415424, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

90 mg (0.3 mmole) of N-(3-nitrobenzyl)adamantane-1,3-diamine and 50 mg (0.24 mmole) of (2S)-1-(chloroacetyl)-4,4-difluoropyrrolidine-2-carbonitrile are dissolved in acetonitrile, to the solution 300 mg (0.75 mmole) of polimer bound 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine (PBEMP) are added. The mixture is sirred at 70° C. for 4 hours, then at room temperature for 20 hours. The scavanger resin is fitered off and the filtrate is evapotared, the residue is purified by column chromatography (chloroform-methanol 6:1). After acidification of the formed oil with ethereal hydrochloride acide the title compound is obtained: 41 mg (29%), m.p.: 226-229° C. 1H-NMR (DMSO-d6): 1.57 (s, 2H), 1.95 (d, 8H), 2.45 (d, 4H), 2.91 (m, 2H), 4.14 (m, 2H), 4.33 (m, 4H), 5.21 (m, 1H), 7.74 (t, 1H), 8.15 (t, 1H), 8.27 (dd, 1H), 8.58 (s, 1H), 9.41 (b, 2H), 9.77 (b, 2H).

Workup

  1. additionare added
  2. waitat room temperature for 20 hours
  3. customthe residue is purified by column chromatography (chloroform-methanol 6:1)
  4. customis obtained

Sources & evidence

ORD record
ord-473d6be12c21426d9579428eb2e94f4e
Source dataset
uspto-grants-2010_01
Patent number
US07652021B2

Reaction notes

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