2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → HCID 53358259, compound

HRID 1805959Notes

Reaction equation

HRID 1805959 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12]([NH:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])(=[O:14])=[O:13])[CH:8]=2)[O:3]1.BrC[C:27]1[CH:28]=[C:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:30]=[CH:31][CH:32]=1.[CH3:39]CN(P1(N(C)CCCN1C)=NC(C)(C)C)CC>C(#N)C>[C:33]1([C:29]2[CH:28]=[CH:27][CH:32]=[CH:31][CH:30]=2)[CH:34]=[CH:35][C:36]([CH2:39][N:15]([CH2:16][C:17]([OH:19])=[O:18])[S:12]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[O:3][C:2]([CH3:1])([CH3:24])[CH2:11][CH2:10]3)(=[O:13])=[O:14])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 38644053-(Bromomethyl)biphenylHCID 58409094Tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate

Product 1

HCID 53358259HCID 53358259, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate (40 mg, 0.113 mmol) in acetonitrile (2 mL) was added 3-(bromomethyl)biphenyl (38.9 mg, 0.158 mmol) and resin-supported BEMP (74.5 mg, 0.164 mmol). The mixture was heated in an oil bath at 90° C. overnight. The reaction mixture was filtered, and the filtrate was concentrated to dryness. The crude mixture was taken in DCM (2 mL) and trifluoroacetic acid was added (1 mL). The mixture was stirred at RT for 1 hr and was concentrated to give a off white residue, which was purified by preparative HPLC using MeCN—H2O-0.1% TFA as the solvent to obtain the product as a white powder (25 mg, 45% in two steps). 1H NMR (400 MHz, CDCl3) δ 7.66-7.61 (m, 2H), 7.60 (d, J=1.4 Hz, 1H), 7.59-7.56 (m, 2H), 7.55 (d, J=1.7 Hz, 1H), 7.49-7.43 (m, 2H), 7.40-7.35 (m, 1H), 7.32 (d, J=8.2 Hz, 2H), 6.89 (dd, J=8.5, 7.2 Hz, 1H), 4.52 (s, 2H), 3.99 (s, 2H), 2.83 (t, J=6.7 Hz, 2H), 1.86 (t, J=6.7 Hz, 2H), 1.38 (s, 6H). LRMS [ESI, MH+] m/z calcd for C26H28NO5S 466.17. found 466.1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. additiontrifluoroacetic acid was added (1 mL)
  4. concentrationwas concentrated
  5. customto give a off white residue, which
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-1d6d57d7285b491eb6a567b9d6b9ceb9
Source dataset
uspto-grants-2013_01
Patent number
US08354548B2

Reaction notes

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