Hydrochloric Acid → HCID 69838978, compound

HRID 1393947Notes

Reaction equation

HRID 1393947 reaction equation
N1C=CN=CC=1[N:7]1[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]1.ClCC([N:18]1[CH2:22][C:21](F)(F)C[C@H:19]1[C:25]#[N:26])=O.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.Cl>C(#N)C.C(OCC)C>[N:18]1[CH:19]=[CH:25][N:26]=[CH:21][C:22]=1[CH:12]1[CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8][NH:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 16778473HCID 16778473, compoundHCID 45081037(2S)-1-(Chloroacetyl)-4,4-difluoropyrrolidine-2-carbonitrile

Product 1

HCID 69838978HCID 69838978, compoundYield 145.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

63 mg of 1-(2-pyrazinyl)-4-amino-piperidine (0.32 mmol) and 62 mg (2S)-1-(2-chloroacetyl)-4,4-difluoro-2-pyrrolidine carbonitrile (0.32 mmol) and 285 mg of polymer-bound 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine (PBEMP) (0.73 mmol) are dissolved in 20 ml dry acetonitrile and stirred at 55° C. for 8 hours. The resin is removed by filtration, the filtrate is concentrated by vacuum and the residue is purified by column chromatography using chloroform—methanol (9:1) as eluent to result an oil, which is treated with hydrochloric acid in diethylether result in 83 mg (60%) of title compound, as white crystals. M.p.: 158-160° C. 1H-NMR (400 MHz, DMSO-d6): δ 1.54 (m, 2H), 2.15 (m, 2H), 2.80-2.95 (m, 4H), 4.20-4.25 (m, 4H), 4.55 (d, 2H,), 5.20 (t, 1H), 7.00 (d, 1H), 7.87 (dd, 1H), 8.50 (d, 1H); 9.38 (br, 2H).

Workup

  1. customThe resin is removed by filtration
  2. concentrationthe filtrate is concentrated by vacuum
  3. customthe residue is purified by column chromatography
  4. customto result an oil, which

Sources & evidence

ORD record
ord-e25258dd802e43668de523ddb67d0def
Source dataset
uspto-grants-2008_03
Patent number
US07348327B2

Reaction notes

Loading…