1,2-Dichloroethane → HCID 68274458, compound

HRID 628990Notes

Reaction equation

HRID 628990 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.CCN(CC)CC.[CH2:29]([O:31][C:32]([C:34]1[C:39]([O:40][CH2:41][CH3:42])=[C:38]([N:43]2[CH2:48][CH2:47][O:46][CH2:45][CH2:44]2)[N:37]=[C:36]([C:49]2[CH:54]=[CH:53][C:52]([NH:55][C:56]([NH:58][C:59]3[CH:64]=[CH:63][C:62]([C:65]([OH:67])=O)=[CH:61][CH:60]=3)=[O:57])=[CH:51][CH:50]=2)[N:35]=1)=[O:33])[CH3:30]>CN(C=O)C>[CH2:29]([O:31][C:32]([C:34]1[C:39]([O:40][CH2:41][CH3:42])=[C:38]([N:43]2[CH2:48][CH2:47][O:46][CH2:45][CH2:44]2)[N:37]=[C:36]([C:49]2[CH:54]=[CH:53][C:52]([NH:55][C:56]([NH:58][C:59]3[CH:64]=[CH:63][C:62]([C:65]([N:19]4[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]4)=[O:67])=[CH:61][CH:60]=3)=[O:57])=[CH:51][CH:50]=2)[N:35]=1)=[O:33])[CH3:30]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 67295436HCID 67295436, compound

Product 1

HCID 68274458HCID 68274458, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (53.7 mg, 1.5 eq.), HOBT (42.9 mg, 1.5 eq.), 1-methyl-piperazine (0.03 ml, 1.5 eq.) and Et3N (0.053 ml, 2.0 eq.) were added to a stirred solution of 2-{4-[3-(4-carboxy-phenyl)-ureido]-phenyl}-5-ethoxy-6-morpholin-4-yl-pyrimidine-4-carboxylic acid ethyl ester (80 mg, 1 eq.) in dry DMF (2 ml) and the mixture reacted overnight at r.t. The mixture was quenched with H2O, extracted with EA, and washed with brine. The crude was purified by chromatography to give a product (34.5 mg, 30%).

Workup

  1. customthe mixture reacted overnight at r.t
  2. customThe mixture was quenched with H2O
  3. extractionextracted with EA
  4. washwashed with brine
  5. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-20d2657d4f3a458cb31165437bddc1a3
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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