Water → 3-bromo-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide

HRID 2410699Notes

Reaction equation

HRID 2410699 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15](=[O:17])[NH2:16])[CH:14]=1)[NH:11][C:10]1[CH:9]=[C:8]([C:18]([OH:20])=O)[CH:7]=[CH:6][C:5]2=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[Br:1][C:2]1[CH:14]=[C:13]([C:15]([NH2:16])=[O:17])[C:12]2[NH:11][C:10]3[C:5]([C:4]=2[CH:3]=1)=[CH:6][CH:7]=[C:8]([C:18]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[O:20])[CH:9]=3

Participants

7

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666048126-bromo-8-carbamoyl-9H-carbazole-2-carboxylic acid

Product 1

HCID 666047593-bromo-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamideYield 79.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

6-Bromo-8-carbamoyl-9H-carbazole-2-carboxylic acid (758 mg, 1.707 mmol, Example 58D) was mixed with morpholine (892 mg, 10.24 mmol), HATU (1947 mg, 5.12 mmol) and DMAP (625 mg, 5.12 mmol) in DMF (8 mL) and stirred for 2 hrs at r.t. The mixture was added slowly to 200 ml H2O while stirring. Resulting mixture was stirred for 10 mins. The resulting yellow precipitate was filtered and air-dried overnight with air-suction to give 546 mg of 3-bromo-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide which was used as such in the next step.

Workup

  1. stirringwhile stirring
  2. customResulting mixture
  3. stirringwas stirred for 10 mins
  4. filtrationThe resulting yellow precipitate was filtered
  5. customair-dried overnight with air-suction

Sources & evidence

ORD record
ord-8241fde27c444a2da30e1c20898cda31
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…