Ethylamine → [2-[2-[1-[[4-[5-[(Ethylamino)carbonyl]-2-methylphenyl]-3,4-dihydro-3-oxopyrazinyl]amino]-1-methylethyl]phenoxy]ethyl]methyl-carbamic acid phenylmethyl ester

HRID 2070754Notes

Reaction equation

HRID 2070754 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([CH3:41])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH2:27][CH2:28][N:29]([CH3:40])[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH3:19])[C:12]1=[O:42].F[B-](F)(F)F.[N:48]1(OC(N(C)C)=[N+](C)C)[C:52]2C=CC=C[C:51]=2N=N1.C(N(C(C)C)C(C)C)C.C(N)C>CN(C=O)C.O>[C:34]1([CH2:33][O:32][C:30](=[O:31])[N:29]([CH2:28][CH2:27][O:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:18]([NH:17][C:13]2[C:12](=[O:42])[N:11]([C:3]3[CH:4]=[C:5]([C:6]([NH:48][CH2:52][CH3:51])=[O:8])[CH:9]=[CH:10][C:2]=3[CH3:1])[CH:16]=[CH:15][N:14]=2)([CH3:19])[CH3:41])[CH3:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 666896944-methyl-3-[3-[[1-methyl-1-[2-[2-[methyl[(phenylmethoxy)carbonyl]amino]ethoxy]phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzoic acid

Product 1

HCID 66689896[2-[2-[1-[[4-[5-[(Ethylamino)carbonyl]-2-methylphenyl]-3,4-dihydro-3-oxopyrazinyl]amino]-1-methylethyl]phenoxy]ethyl]methyl-carbamic acid phenylmethyl esterYield 750.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 4-methyl-3-[3-[[1-methyl-1-[2-[2-[methyl[(phenylmethoxy)carbonyl]amino]ethoxy]phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzoic acid (Example 220d, 0.14 g) in DMF (3 mL) were added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.158 g) followed by N-ethyldiisopropylamine (0.212 mL) and the reaction stirred for 15 min before ethylamine (0.032 mL) was added and the reaction stirred for 3 h. The reaction was diluted with water and the aqueous layer extracted with ethyl acetate. The combined organics were dried (Na2 SO4) and solvents removed in vacuo to give the subtitle product (1.10 g).

Workup

  1. additionwas added
  2. extractionthe aqueous layer extracted with ethyl acetate
  3. customThe combined organics were dried (Na2 SO4) and solvents
  4. customremoved in vacuo

Sources & evidence

ORD record
ord-0127f8a20a024ccdb78099d2ecfede22
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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