1-Hydroxybenzotriazole → (2-{3-Chloro-5-[(2-cyano-ethyl)-(tetrahydro-furan-2-ylmethyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester

HRID 2268604Notes

Reaction equation

HRID 2268604 reaction equation
[C:1]([O:5][C:6]([N:8]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[O:69]1[CH2:73][CH2:72][CH2:71][CH:70]1[CH2:74][NH:75][CH2:76][CH2:77][C:78]#[N:79]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:15](=[O:17])[N:75]([CH2:76][CH2:77][C:78]#[N:79])[CH2:74][CH:70]2[CH2:71][CH2:72][CH2:73][O:69]2)[CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:22]1[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27793283-[(Tetrahydrofuran-2-ylmethyl)amino]propanenitrileHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

Product 1

HCID 69948292(2-{3-Chloro-5-[(2-cyano-ethyl)-(tetrahydro-furan-2-ylmethyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl esterYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.060 g), TBTU (0.096 g) and HOBT (0.030 g) in DMF (1 ml) was added DIPEA (0.052 ml) followed by 3-[(tetrahydro-furan-2-ylmethyl)-amino]-propionitrile (0.047 g) after 15 min. The reaction was stirred at room temperature for 96 h, and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.078 g) was obtained as a brown oil by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-049c9ee70cf34471943abadd9f445d0b
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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