Triethylamine → HCID 44159737, compound

HRID 1886966Notes

Reaction equation

HRID 1886966 reaction equation
[NH2:1][CH:2]1[C:8]2=[N:9][C:10]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][N:15]=3)=[CH:11][C:12](=[O:13])[N:7]2[CH2:6][CH2:5][O:4][CH2:3]1.[C:20]([O:24][C:25]([N:27]1[CH2:36][CH2:35][C:34]2[C:29](=[CH:30][C:31]([C:37](O)=[O:38])=[CH:32][CH:33]=2)[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[C:20]([O:24][C:25]([N:27]1[CH2:36][CH2:35][C:34]2[C:29](=[CH:30][C:31]([C:37](=[O:38])[NH:1][CH:2]3[C:8]4=[N:9][C:10]([C:14]5[CH:19]=[CH:18][N:17]=[CH:16][N:15]=5)=[CH:11][C:12](=[O:13])[N:7]4[CH2:6][CH2:5][O:4][CH2:3]3)=[CH:32][CH:33]=2)[CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 189883742-((Tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acidHCID 68626960HCID 68626960, compound

Product 1

HCID 44159737HCID 44159737, compoundYield 38.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.080 g (0.31 mmol) of (+/−)-9-Amino-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4-a-diaza-benzocyclohepten-4-one dissolved in 2.60 mL of dimethylformamide was added 0.086 g (0.31 mmol) of 3,4-dihydro-1H-isoquinoline-2,7-dicarboxylic acid 2-tert-butyl ester. To the resulting mixture was added 60 μL (0.37 mmol) of diethyl cyanophosphonate and 40 μL (0.31 mmol) of triethylamine at 0° C. The resulting mixture was stirred at room temperature for 15 hours. Water and ethyl acetate were added and the mixture was stirred. The resulting residue was filtered, washed with water, ethyl acetate and diethyl ether to afford 0.062 g (38%) of the pure product as a white powder.

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe resulting residue was filtered
  3. washwashed with water, ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-073d483f88a04d54866a02d9abd78431
Source dataset
uspto-grants-2013_08
Patent number
US08501728B2

Reaction notes

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