Triethylamine → HCID 13922915, compound

HRID 979483Notes

Reaction equation

HRID 979483 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH2:16][CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:37][CH3:38])=[C:32]([O:35][CH3:36])[CH:33]=3)[N:28]=[CH:27][N:26]=2)[CH2:21][CH2:20]1.[C:39]([N:46]1[CH2:53][CH2:52][CH2:51][C@H:47]1[C:48](O)=[O:49])([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].C(N(CC)CC)C>C(#N)C>[C:39]([N:46]1[CH2:53][CH2:52][CH2:51][C@H:47]1[C:48]([NH:16][CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:37][CH3:38])=[C:32]([O:35][CH3:36])[CH:33]=3)[N:28]=[CH:27][N:26]=2)[CH2:21][CH2:20]1)=[O:49])([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 13922912HCID 13922912, compound

Product 1

HCID 13922915HCID 13922915, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N'-dicyclohexylcarbodiimide (0.53 g) was added to a mixture of 4-(2-aminoethyl)-1-(6,7-dimethoxyquinazolin-4-yl)piperidine.2HCl (1.2 g), Boc-L-proline (1.1 g), triethylamine (0.72 ml) and acetonitrile (20 ml). The mixture was stirred at room temperature for 12 hours and filtered. The filtrate was dried and concentrated under reduced pressure. The residue was partitioned between an aqueous solution of 10% NaHCO3 and chloroform. The organic layer was dried over anhydrous magnesium sulfate, concentrated and purified by using a 40 g silica gel column to give 4-{2-(Boc-L-prolylamino)ethyl}-1-(6,7-dimethoxyquinazolin-4-yl)piperidine (1.23 g; 93%).

Workup

  1. filtrationfiltered
  2. customThe filtrate was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between an aqueous solution of 10% NaHCO3 and chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-c9455c9fb54f4037b1fbcad6e5395bc3
Source dataset
uspto-grants-1987_05
Patent number
US04668683

Reaction notes

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