1,2-Dichloroethane → HCID 67114091, compound

HRID 2284194Notes

Reaction equation

HRID 2284194 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][N: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=N1.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]=[N:14]2)=[CH:28][CH:29]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 120924-(Dimethylamino)benzoic acidHCID 880121H-Indazol-5-amineHCID 45867662HCID 45867662, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 67114091HCID 67114091, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 371 was prepared according to the general procedure described in Scheme IV. Preparation of 4-(dimethylamino)-N-(1H-indazol-5-yl)benzamide: 1H-Indazol-5-amine (200 mg, 1.50 mmol), hydroxybenzotriazole (20 mg, 0.15 mmol), triethylamine (0.23 mL, 1.65 mmol), and 4-(dimethylamino)benzoic acid (273 mg, 1.65 mmol) were taken up in DMF (7.5 mL) and stirred. EDC (317 mg, 1.65 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 solid was dried under vacuum to give 410 mg (97%) of the product as a brown solid.

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 solid was dried under vacuum

Sources & evidence

ORD record
ord-4dd921449ed24d6d8a545057efb85b77
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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