Triethylamine → HCID 178458433, compound

HRID 2236742Notes

Reaction equation

HRID 2236742 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:11][CH2:12][CH2:13][CH3:14])=[C:8]([OH:10])[CH:9]=1.C(N(CC)CC)C.CO[CH:24]=[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([N:35]3[CH:39]=[CH:38][CH:37]=[CH:36]3)[CH:33]=2)[C:28](=[O:40])[NH:27][C:26]1=[O:41]>CN(C)C=O>[OH:10][C:8]1[CH:9]=[C:4]([CH:5]=[CH:6][C:7]=1[O:11][CH2:12][CH2:13][CH3:14])[CH2:3][NH:2][CH:24]=[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([N:35]3[CH:39]=[CH:38][CH:37]=[CH:36]3)[CH:33]=2)[C:28](=[O:40])[NH:27][C:26]1=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 426258325-(Aminomethyl)-2-propoxyphenol hydrochlorideHCID 686931254-methoxymethylene-6-pyrrol-1-yl-4H-isoquinoline-1,3-dione

Product 1

HCID 178458433HCID 178458433, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-aminomethyl-2-propoxy-phenol hydrochloride (109 mg, 0.50 mmole), 4 mL of N,N-dimethylformamide and triethylamine (75 μL, 0.54 mmole) is stirred for 15 minutes. Then (4-methoxymethylene-6-pyrrol-1-yl-4H-isoquinoline-1,3-dione (134 mg, 0.50 mmole) is added and the reaction mixture stirred for one hour. The reaction mixture is evaporated to dryness, taken up in 5% methanol in chloroform and passed through a short pad of Florisil eluting with 5% methanol in chloroform. The eluate is evaporated in vacuo and treated with acetonitrile, filtered and dried to give a beige solid, 94 mg, (45%), mp 215-216° C. dec; MS (ES+): m/z 418.2 (M+H).

Workup

  1. stirringthe reaction mixture stirred for one hour
  2. customThe reaction mixture is evaporated to dryness
  3. customThe eluate is evaporated in vacuo
  4. additiontreated with acetonitrile
  5. filtrationfiltered
  6. customdried
  7. customto give a beige solid, 94 mg, (45%), mp 215-216° C. dec

Sources & evidence

ORD record
ord-1002e16325fc4f38b7a7c03646426111
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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