2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → HCID 53358258, compound

HRID 1805958Notes

Reaction equation

HRID 1805958 reaction equation
BrC[C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:15]CN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[CH3:33][C:34]1([CH3:56])[CH2:43][CH2:42][C:41]2[C:36](=[CH:37][CH:38]=[C:39]([S:44]([NH:47][CH2:48][C:49]([O:51]C(C)(C)C)=[O:50])(=[O:46])=[O:45])[CH:40]=2)[O:35]1>C(#N)C>[C:9]1([C:5]2[CH:4]=[CH:3][CH:8]=[CH:7][CH:6]=2)[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[CH2:15][N:47]([CH2:48][C:49]([OH:51])=[O:50])[S:44]([C:39]1[CH:40]=[C:41]2[C:36](=[CH:37][CH:38]=1)[O:35][C:34]([CH3:56])([CH3:33])[CH2:43][CH2:42]2)(=[O:46])=[O:45]

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 53358258HCID 53358258, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a Wheaton vial containing 3-(bromomethyl)biphenyl (22.2 mg, 0.090 mmol) and resin-supported BEMP (52 mg, 0.095 mmol) was added a solution of tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate (18 mg, 0.05 mmol) in acetonitrile (1 mL). The mixture was heated to 90° C. and shaken vigorously for two days. The reaction mixture was filtered, and the filtrate was concentrated. The crude product was taken in dichloromethane (0.5 mL) and trifluroacetic acid (0.5 mL) was added. The mixture was shaken for 4 hours at room temperature. It was concentrated and the residue was purified by prep HPLC to obtain the product (15.3 mg, 66% yield in two steps). 1H NMR (600 MHz, DMSO/CDCl3) δ 7.52-7.46 (m, 1H), 7.46-7.41 (m, 2H), 7.41-7.33 (m, 5H), 7.23 (d, J=7.4 Hz, 2H), 7.19-7.14 (m, 1H), 6.77 (d, J=9.1 Hz, 1H), 4.40 (s, 2H), 3.63 (s, 2H), 2.75 (t, J=6.4 Hz, 2H), 1.82 (t, J=6.5 Hz, 2H), 1.34 (s, 6H). LRMS [ESI, MH+] m/z calcd for C26H28NO5S 466.17, found 466.22.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additiontrifluroacetic acid (0.5 mL) was added
  4. stirringThe mixture was shaken for 4 hours at room temperature
  5. concentrationIt was concentrated
  6. customthe residue was purified by prep HPLC
  7. customto obtain the product (15.3 mg, 66% yield in two steps)

Sources & evidence

ORD record
ord-707123602d254e1bb770b8ee0c988769
Source dataset
uspto-grants-2013_01
Patent number
US08354548B2

Reaction notes

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