Triethylamine → HCID 57970179, compound

HRID 1666651Notes

Reaction equation

HRID 1666651 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:25]([N:32]1[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C(O)(C)C>[CH2:25]([N:32]1[CH2:36][CH2:35][C@H:34]([NH:37][C:2]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13]3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:33]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidineHCID 24752963950666-26-9

Product 1

HCID 57970179HCID 57970179, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of t-butyl 4-(2-chloroquinazolin-4-yl)piperazine-1-carboxylate (30 g) synthesized in the same manner as in Example 1, (S)-1-benzyl-3-aminopyrrolidine (15 g), triethylamine (8.7 g), and isopropyl alcohol (43 mL) was heated to reflux for 40 h. The reaction mixture was concentrated under reduced pressure, then water was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried with anhydrous magnesium sulfate, concentrated, and then purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=4:1) to obtain t-butyl 4-(2-((S)-1-benzylpyrrolidin-3-ylamino)quinazolin-4-yl)piperazine-1-carboxylate (26 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 40 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionwater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-746b17b2df514c50bcf2c9f1b55e422c
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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