1-Hydroxybenzotriazole → N-(3-(pyrimidin-5-yl)-phenyl)-2,3-dimethyl-1H-indole-7-carboxamide

HRID 1835462Notes

Reaction equation

HRID 1835462 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=2[C:12]([OH:14])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[N:37]1[CH:42]=[C:41]([C:43]2[CH:44]=[C:45]([CH:47]=[CH:48][CH:49]=2)[NH2:46])[CH:40]=[N:39][CH:38]=1>ClCCl>[N:37]1[CH:42]=[C:41]([C:43]2[CH:44]=[C:45]([NH:46][C:12]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[NH:3][C:2]([CH3:1])=[C:10]4[CH3:11])=[O:14])[CH:47]=[CH:48][CH:49]=2)[CH:40]=[N:39][CH:38]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 37026102,3-Dimethyl-7-indolecarboxylic acidHCID 71620493-Pyrimidin-5-ylaniline

Product 1

HCID 23503684N-(3-(pyrimidin-5-yl)-phenyl)-2,3-dimethyl-1H-indole-7-carboxamideYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2,3-dimethylindole-7-carboxylic acid (95 mg) and 1-hydroxybenzotriazole (81 mg) in dichloromethane (3 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg), and the mixture was stirred for 5 minutes. After adding 3-(pyrimidin-5-yl)aniline (94 mg) and 4-dimethylinopyridine (92 mg), the mixture was stirred for 24 hours. The mixture was diluted with dichloromethane and washed with water and brine. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 3% methanol in dichloromethane to give N-(3-(pyrimidin-5-yl)-phenyl)-2,3-dimethyl-1H-indole-7-carboxamide (117 mg, 68.4%).

Workup

  1. stirringthe mixture was stirred for 24 hours
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography
  6. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-3c26dbca05024175b655374961393faf
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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