2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → HCID 44200771, compound

HRID 1254655Notes

Reaction equation

HRID 1254655 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][NH:9][C:10](=O)[C@H:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([Cl:25])[C:18]=2[CH3:26])[C:12]([OH:15])([CH3:14])[CH3:13])=[O:7])=[CH:4][CH:3]=1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC>C1COCC1>[Cl:25][C:19]1[C:18]([CH3:26])=[C:17]([NH:16][C@@H:11]([C:10]2[O:7][C:6]([C:5]3[CH:28]=[CH:29][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:8][N:9]=2)[C:12]([OH:15])([CH3:14])[CH3:13])[CH:22]=[CH:21][C:20]=1[C:23]#[N:24]

Participants

4

Reactant 2

HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine2×HCID 67007126HCID 67007126, compound2×

Product 1

HCID 44200771HCID 44200771, compoundYield 334.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude material of (R)-4-chloro-N′-(2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxy-3-methylbutanoyl)benzohydrazide (intermediate 15a) (230 mg, 0.53 mmol) was added to THF (50 mL) stirred at room temperature. PS-BEMP (721 mg, 1.59 mmol base) was added to the solution followed by slow addition of p-TSCl (111 mg, 0.58 mmol). The reaction mixture was stirred for 1 h and the progress of the reaction was monitored by TLC. After the completion of the reaction the BEMP reagent was filtered off and the solution concentrated to get the crude material. The crude material was chromatographed with hexanes:EtOAc (6:4) to provide the product (740 mg): 1H NMR (500 MHz; CDCl3, δ in ppm) 7.95 (d, J=9 Hz, 2H), 7.50 (d, J=9 Hz, 2H), 7.39 (d, J=9 Hz, 1H), 6.63 (d, J=9 Hz, 1H), 5.37 (d, J=9 Hz, 1H), 4.74 (d, J=9 Hz, 1H), 2.36 (s, 3H), 1.52 (s, 3H), 1.36 (s, 3H).

Workup

  1. additionfollowed by slow addition of p-TSCl (111 mg, 0.58 mmol)
  2. stirringThe reaction mixture was stirred for 1 h
  3. filtrationwas filtered off
  4. concentrationthe solution concentrated
  5. customto get the crude material
  6. customThe crude material was chromatographed with hexanes:EtOAc (6:4)

Sources & evidence

ORD record
ord-b47b2a01a4604fa28b715dbff475406f
Source dataset
uspto-grants-2013_06
Patent number
US08455525B2

Reaction notes

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