Dimethylformamide → HCID 18320659, compound

HRID 1699522Notes

Reaction equation

HRID 1699522 reaction equation
[C:1]([CH:4]([NH:16][C:17](=[O:33])[NH:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:20]=1)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6])(=[O:3])[NH2:2].Br[CH2:35][CH2:36][CH2:37][N:38]1[C:42](=[O:43])[C:41]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:40]2[C:39]1=[O:48].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C(OCC)C>[C:1]([CH:4]([NH:16][C:17](=[O:33])[NH:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:20]=1)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:35][CH2:36][CH2:37][N:38]2[C:42](=[O:43])[C:41]3[C:40](=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:39]2=[O:48])[CH:8]=1)=[O:6])(=[O:3])[NH2:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 15550598HCID 15550598, compound

Product 1

HCID 18320659HCID 18320659, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 0.10 g (0.223 mmol) of the product from step d), 0.15 g (0.56 mmol) of N-(3-bromopropyl)phthalimide, 0.10 g (0.72 mmol) of K2CO3 and 1.5 ml of DMF. The flask was sealed and heated to 65° C. for 5 hours. The reaction mixture was partitioned between 10 ml of EtOAc and 10 ml of water. The organic phase was collected and the aqueous phase was extracted with an additional 10 ml of EtOAc. The combined organic phases were washed with water and brine. The organic phase was evaporated to give a yellowish solid. The solid was suspended in 20 ml of diethyl ether and stirred for 30 minutes. The precipitate was allowed to settle and the ethereal phase was removed. The residual precipitate was dried in vacuum to give 100 mg (70%) of the sub-title product.

Workup

  1. customThe flask was sealed
  2. customThe reaction mixture was partitioned between 10 ml of EtOAc and 10 ml of water
  3. customThe organic phase was collected
  4. extractionthe aqueous phase was extracted with an additional 10 ml of EtOAc
  5. washThe combined organic phases were washed with water and brine
  6. customThe organic phase was evaporated
  7. customto give a yellowish solid
  8. customthe ethereal phase was removed
  9. customThe residual precipitate was dried in vacuum

Sources & evidence

ORD record
ord-3884f8530ea54f08823c99848c02b2e6
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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