Acetonitrile → 1-Benzyl-1H-indole-3-carboxylic acid pyrimidin-4-ylamide

HRID 1685568Notes

Reaction equation

HRID 1685568 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([OH:19])=O)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[N:22][CH:21]=1.CC#N>O=S(Cl)Cl.CN1C(=O)CCC1>[N:20]1[CH:25]=[CH:24][C:23]([NH:26][C:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=2)=[O:19])=[N:22][CH:21]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 336711-benzyl-1H-indole-3-carboxylic acidHCID 689584-Aminopyrimidine

Product 1

HCID 595139721-Benzyl-1H-indole-3-carboxylic acid pyrimidin-4-ylamide

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

1-Benzylindole-3-carboxylic acid (25.9 mg, 96 mmol) was dissolved in SOCl2 (1 mL) and the mixture was stirred for 30 min before the volatiles were removed in vacuo. The residue was dissolved in MeCN (200 μL) and added to a solution of pyrimidin-4-yl-amine (10 mg, 105 mmol) in NMP (200 μL). The reaction mixture was stirred 16 hours at room temperature before the MeCN was removed in vacuo. The residue was purified using HPLC method D to give title compound. HPLC-MS (Method A): m/z=329 (M+1); Rt=3.3 min.

Workup

  1. customwere removed in vacuo
  2. dissolutionThe residue was dissolved in MeCN (200 μL)
  3. customwas removed in vacuo
  4. customThe residue was purified

Sources & evidence

ORD record
ord-6040cf5de7764e80bd83da69ce4e710d
Source dataset
uspto-grants-2012_04
Patent number
US08148413B2

Reaction notes

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