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 1697336Notes

Reaction equation

HRID 1697336 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 (Na2SO4) 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. dry with materialThe combined organics were dried (Na2SO4) and solvents
  4. customremoved in vacuo

Sources & evidence

ORD record
ord-faa28f00c3164c07b4fc6ce844593484
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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