1,2-Dichloroethane → HCID 67297756, compound

HRID 628985Notes

Reaction equation

HRID 628985 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH:15]([CH2:18][CH3:19])[CH2:16][CH3:17].CCN(CC)CC.[CH2:27]([O:29][C:30]1[C:31]([C:58]([OH:60])=O)=[N:32][C:33]([C:42]2[CH:47]=[CH:46][C:45]([NH:48][C:49]([NH:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)=[O:50])=[CH:44][CH:43]=2)=[N:34][C:35]=1[N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1)[CH3:28]>CN(C=O)C>[CH2:16]([N:15]([CH2:18][CH3:19])[C:58]([C:31]1[C:30]([O:29][CH2:27][CH3:28])=[C:35]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[N:34]=[C:33]([C:42]2[CH:47]=[CH:46][C:45]([NH:48][C:49]([NH:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)=[O:50])=[CH:44][CH:43]=2)[N:32]=1)=[O:60])[CH3:17]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8021DiethylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 67295473HCID 67295473, compound

Product 1

HCID 67297756HCID 67297756, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (50 mg, 1.5 eq.), HOBT (40 mg, 1.5 eq.), Et2NH (0.0275 ml, 1.5 eq.) and Et3N (0.05 ml, 2.0 eq.) were added to a stirred solution of 5-ethoxy-6-morpholin-4-yl-2-[4-(3-phenyl-ureido)-phenyl]-pyrimidine-4-carboxylic acid (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 (43 mg, 48%).

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-53c0d73ef6a34053a3f61ec17e168a09
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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