Diisopropylethylamine → HCID 86591333, compound

HRID 1270205Notes

Reaction equation

HRID 1270205 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)(OC(C)(C)C)=O.ClC1[N:16]=[C:17]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])[C:18]2[CH:24]=[CH:23][CH:22]=[N:21][C:19]=2[N:20]=1.C(N(CC)C(C)C)(C)C>C(O)CCC>[Cl:34][C:28]1[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=1[CH2:26][NH:25][C:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[N:21][C:19]=2[N:20]=[C:1]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[N:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 18449305HCID 18449305, compound

Product 1

HCID 86591333HCID 86591333, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Boc-piperazine (122 mg, 0.65 mmol) was added to the solution of (2-Chloro-pyrido[2,3-d]pyrimidin-4-yl)-(2,4-dichloro-benzyl)-amine(185 mg, 0.54 mmol) and N,N-diisopropylethylamine (145 μL, 0.82 mmol) in n-butanol (2 mL). The reaction mixture was stirred at 85° for 10 h. All starting material was consumed as seen on HPLC. The reaction mixture was concentrated at room temperature under vacuo. The resulting residue was suspended in 2 mL of TFA-CH2Cl2 (1:1) mixture and stirred at room temperature for 45 minutes. The reaction mixture was concentrated in vacuo, diluted with saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with CH2Cl2 (2×10 mL), dried (Na2SO4) and concentratd to furnish (2,4-Dichloro-benzyl)-(2-piperazin-1-yl-pyrido[2,3-d]pyrimidin-4-yl)-amine(210 mg) as pale brown oil. The crude was carried forward as such in the next reaction.

Workup

  1. customwas consumed
  2. concentrationThe reaction mixture was concentrated at room temperature under vacuo
  3. stirringstirred at room temperature for 45 minutes
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additiondiluted with saturated aqueous sodium bicarbonate solution
  6. extractionThe aqueous layer was extracted with CH2Cl2 (2×10 mL)
  7. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-5c3a8ee0e53d4ab3b34140ede3ebd062
Source dataset
uspto-grants-2007_04
Patent number
US07202249B2

Reaction notes

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