Dichloromethane → HCID 15887790, compound

HRID 1637886Notes

Reaction equation

HRID 1637886 reaction equation
CC[N:3]([CH2:6][CH3:7])[CH2:4][CH3:5].C1CCC(N=[C:15]=[N:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)CC1.[CH:23]1[CH:24]=[CH:25]C2N(O)N=N[C:27]=2[CH:28]=1.[C:33]([NH:36][C:37]1[CH:42]=[CH:41][C:40](/[CH:43]=[CH:44]/[C:45]([OH:47])=O)=[CH:39][CH:38]=1)(=[O:35])[CH3:34].[CH2:48](Cl)Cl>C(Cl)Cl.CO>[O:47]=[C:45]([N:3]1[CH2:4][CH2:5][C:48]2[C:18]3[C:17](=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:16][C:15]=2[CH:6]1[C:7]1[CH:25]=[CH:24][CH:23]=[CH:28][CH:27]=1)/[CH:44]=[CH:43]/[C:40]1[CH:39]=[CH:38][C:37]([NH:36][C:33](=[O:35])[CH3:34])=[CH:42][CH:41]=1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 53571557152-04-7

Product 1

HCID 15887790HCID 15887790, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of Intermediate 1 (0.2 g, 0.81 mmol) in 40 mL of DCM were added Et3N (0.13 mL, 1.1 equiv.), DCC (0.18 g, 1.1 equiv.), HOBT (0.12 g, 1.1 equiv.) and (E)-3-(4-acetylaminophenyl)acrylic acid (0.18 g, 1.1 equiv.). After 24 hours of stirring at rt the reaction was judged to be completed by tlc monitoring (SiO2, DCM:MeOH 95:5) and was quenched with 150 mL of water. A white solid precipitated out and was filtered off. The filtrate was extracted with DCM, washed with brine (5 mL), dried over MgSO4 and concentrated in vacuo. Flash chromatography on a 2.5×25 cm2 column of silica gel using DCM:MeOH (98:2) as eluting solvent and removal of the solvent in vacuo gave the title compound (0.18 g, 51%) as yellow crystals after recrystallization from 2-propanol:pentane. MP: 177-180° C.

Workup

  1. customwas quenched with 150 mL of water
  2. customA white solid precipitated out and
  3. filtrationwas filtered off
  4. extractionThe filtrate was extracted with DCM
  5. washwashed with brine (5 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. washas eluting
  9. customsolvent and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-bac2f58456a14119b44d5006b24e913d
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

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