1,2-Dichloroethane → HCID 67112964, compound

HRID 2284192Notes

Reaction equation

HRID 2284192 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1[CH:20]=[CH:19][C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[CH:13]3)=[O:8])=[CH:5][CH:4]=1.[NH:22]1[C:30]2[C:25](=[CH:26][C:27](N)=[CH:28][CH:29]=2)C=C1.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.CN(C)C1C=CC(C(O)=O)=CC=1.C(Cl)CCl>CN(C=O)C.O>[NH2:22][C:30]1[CH:25]=[CH:26][C:27]([N:15]2[C:16]3[C:12](=[CH:11][C:10]([NH:9][C:7](=[O:8])[C:6]4[CH:5]=[CH:4][C:3]([N:2]([CH3:21])[CH3:1])=[CH:20][CH:19]=4)=[CH:18][CH:17]=3)[CH:13]=[CH:14]2)=[CH:28][CH:29]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 120924-(Dimethylamino)benzoic acidHCID 788675-AminoindoleHCID 67113114HCID 67113114, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 67112964HCID 67112964, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 369 was prepared according to the general procedure described in Scheme IV. Preparation of 4-(dimethylamino)-N-(1H-indol-5-yl)benzamide: 1H-indol-5-amine (200 mg, 1.51 mmol), hydroxybenzotriazole (204 mg, 1.51 mmol), triethylamine (0.23 mL, 1.66 mmol), and 4-(dimethylamino)benzoic acid (275 mg, 1.66 mmol) were taken up in DMF (7.5 mL) and stirred. EDC (319 mg, 1.66 mmol) was added to the solution last. After the addition, the solution was stirred at room temperature for 4 h. Water was then added to the solution and stirred for 10 min. The formed precipitate was filtered and washed well with water, followed by hexanes. The grayish solid was dried under vacuum to give 393 mg (93%) of the product.

Workup

  1. additionAfter the addition
  2. stirringthe solution was stirred at room temperature for 4 h
  3. stirringstirred for 10 min
  4. filtrationThe formed precipitate was filtered
  5. washwashed well with water
  6. customThe grayish solid was dried under vacuum

Sources & evidence

ORD record
ord-800de43a092f43aaa281ded717b8b36c
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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