Dimethylformamide → HCID 15948107, compound

HRID 550772Notes

Reaction equation

HRID 550772 reaction equation
[ClH:1].CN(C)[CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[N:9][CH2:10][CH3:11].CN1CCO[CH2:16][CH2:15]1.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[C:29](O)=O)[CH:22]=[CH:21]1.[OH2:32].O[N:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2N=N1.C[N:44](C=O)C>O>[NH2:44][C:8]1[N:7]=[C:6]([C:40]2[CH:41]=[CH:42][CH:37]=[C:38]([NH:34][C:29]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:28]=3[NH:20][CH:21]=[CH:22]4)=[O:32])[CH:39]=2)[C:5]2[C:10](=[CH:11][CH:15]=[C:16]([Cl:1])[CH:4]=2)[N:9]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 742811H-Indole-7-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 15948107HCID 15948107, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

106.2 mg of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) and 56 mg of N-methylmorpholine are added to a solution of 73.6 mg of 1H-indole-7-carboxylic acid and 67.9 mg of 1-hydroxybenzotriazole hydrate (HOBt) in 1 ml of DMF. The mixture is stirred at room temperature for 1 hour. 100 mg of “6” are then added, and the mixture is stirred for 16 hours. The mixture is stirred into 10 ml of water, the precipitated material is separated off and washed with water. The residue is boiled once with 10 ml of acetonitrile/water and dried, giving 132 mg of 2-amino-6-chloro-4-[3-(indol-7-ylcarbonylamino)phenyl]quinazoline (“A11”).

Workup

  1. addition100 mg of “6” are then added
  2. stirringthe mixture is stirred for 16 hours
  3. customthe precipitated material is separated off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5f8b16501e574f31a89c9e1c45e55914
Source dataset
uspto-grants-2011_05
Patent number
US07947696B2

Reaction notes

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