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1,2-Dichloroethane → HCID 57345388, compound

HRID 1616801
Notes
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Reaction equation

HRID 1616801 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[N:7]([CH3:14])[CH:6]=[C:5]2[CH:15]([CH3:17])[CH3:16].[NH2:18][CH2:19][C:20]1[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=1[CH3:26].C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH:18][CH2:19][C:20]3[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=3[CH3:26])=[O:13])[CH:10]=1)[N:7]([CH3:14])[CH:6]=[C:5]2[CH:15]([CH3:17])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 678162465-bromo-1-methyl-3-(1-methylethyl)-1H-indole-7-carboxylic acid

Product 1

HCID 57345388HCID 57345388, compound
Yield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 5-bromo-1-methyl-3-(1-methylethyl)-1H-indole-7-carboxylic acid (300 mg, 1.013 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (280 mg, 1.484 mmol) and HOAt (200 mg, 1.469 mmol) in DMF (15 mL) was added N-methylmorpholine (170 μL, 1.546 mmol) and EDC free base (310 mg, 1.997 mmol). The reaction was stirred for 18 h at RT. LCMS showed that the reaction was complete. The reaction was evaporated to near dryness under vacuum. Water (˜15 mL) was added and the solids which precipitated out were triturated, filtered and dried under vacuum. LCMS indicated that the solids were only 87% pure. The solid was partially dissolved in CH2Cl2. Noticed that the product began to crystallize out. Slowly added an equal volume of hexanes, triturated, filtered and dried under vacuum to give the product 5-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-methyl-3-(1-methylethyl)-1H-indole-7-carboxamide (188 mg, 0.437 mmol, 43.1% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=11.50 (br. s., 1H), 8.54 (t, J=4.8 Hz, 1H), 7.75 (d, J=1.8 Hz, 1H), 7.14 (s, 1H), 7.09 (d, J=2.0 Hz, 1H), 5.87 (s, 1H), 4.31 (d, J=5.1 Hz, 2H), 3.65 (s, 3H), 3.11 (dt, J=6.9, 13.5 Hz, 1H), 2.22 (s, 3H), 2.12 (s, 3H), 1.26 (d, J=6.8 Hz, 6H). MS (ES)+ m/e 429.9 [M+H]+.

Workup

  1. customThe reaction was evaporated
  2. additionWater (˜15 mL) was added
  3. customthe solids which precipitated out
  4. customwere triturated
  5. filtrationfiltered
  6. customdried under vacuum
  7. dissolutionThe solid was partially dissolved in CH2Cl2
  8. customto crystallize out
  9. additionSlowly added an equal volume of hexanes
  10. customtriturated
  11. filtrationfiltered
  12. customdried under vacuum

Sources & evidence

ORD record
ord-c075624d022a4486932ab3311df41465
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765792B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes