Dichloromethane → HCID 69301241, compound

HRID 131254Notes

Reaction equation

HRID 131254 reaction equation
C([C:5]1[CH:13]=[C:12]([N:14]([C:22](=[O:24])[CH3:23])[CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:33]>>[ClH:33].[C:22]([N:14]([C:12]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:13]=1)[CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)(=[O:24])[CH3:23]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 69298930HCID 69298930, compound

Product 1

HCID 69301241HCID 69301241, compound

Procedure

To a solution of tert-butyl 4-[N-acetyl-N-[2-(1-pyrrolidinyl)ethyl]amino]-benzoic acid (37 mg, compound obtained in Reference Example 107) in methylene chloride (0.2 mL) is added trifluoroacetic acid (0.2 mL), and the mixture is shaken at room temperature for one day. The reaction mixture is concentrated and the residue is subjected to azeotropic distillation successively with chloroform, 4N HCl-dioxane and chloroform to give 4-[N-acetyl-N-[2-(1-pyrrolidinyl)ethyl]amino]benzoate hydrochloride. The product and 1 (3-ethoxybenzyl)-4-piperazin-1-yl-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride are treated in the same manner (condensation reaction) as described in Example 3 and then the resultant product is treated in the same manner as described in Example 4(3) to give 1-(3-ethoxybenzyl)-4-[4-[4-[N-acetyl-N-[2-(1-pyrrolidinyl)ethyl]amino]benzoyl]piperazin-1-yl]-1H-pyrazolo[3,4-d]pyrimidine hydrochloride (15 mg, yield; 21%) as an amorphous powder. MS (APCI) m/z; 597 [M+H]+

Workup

  1. concentrationThe reaction mixture is concentrated
  2. distillationthe residue is subjected to azeotropic distillation successively with chloroform, 4N HCl-dioxane and chloroform

Sources & evidence

ORD record
ord-a391d22ee9104816a4fb81c626658d8e
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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