2-Methylbenzamide → (+/-)-N-(3-amino-propyl)-N-[1-(3-benzyl-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propyl]-4-methyl-benzamide

HRID 1823693Notes

Reaction equation

HRID 1823693 reaction equation
C1(C)C(C(N)=O)=CC=CC=1.C(OC(=O)[NH:17][CH2:18][CH2:19][CH2:20][N:21]([CH:31]([C:35]1[N:44]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:43](=[O:52])[C:42]2[C:37](=[N:38][CH:39]=[CH:40][N:41]=2)[N:36]=1)[CH:32]([CH3:34])[CH3:33])[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)(C)(C)C>C(O)(C(F)(F)F)=O.O.ClCCl>[NH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH:31]([C:35]1[N:44]([CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:43](=[O:52])[C:42]2[C:37](=[N:38][CH:39]=[CH:40][N:41]=2)[N:36]=1)[CH:32]([CH3:34])[CH3:33])[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 107042-MethylbenzamideHCID 69314695{3-[[1-(3-Benzyl-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propyl]-(4-methyl-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 22172580(+/-)-N-(3-amino-propyl)-N-[1-(3-benzyl-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propyl]-4-methyl-benzamideYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22392675Trifluoroacetic acid waterSolvent

Procedure

Formula I where R2 and R3 are H; R5 is Benzyl; R6 is Isopropyl; R6′ is H; R7 is 3-Amino-propyl-; R8 is —C(O)—R9 where R9 is p-Methyl-phenyl-; X and Y are —C═; and W and Z are —N═: The toluamide, {3-[[1-(3-benzyl-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propyl]-(4-methyl-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester, was then dissolved in TFA/H2O (95/5) (50 mL) and stirred at room temperature for 1 hour, after which it was diluted with dichloromethane, washed with saturated sodium bicarbonate, water and brine, and dried over sodium sulfate. Concentration of the dichloromethane solution gave the title product (±)-N-(3-amino-propyl)-N-[1-(3-benzyl-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propyl]-4-methyl-benzamide as a white solid (150 mg, 98.0%). MS (Cl) M/E: 485.2.

Workup

  1. washwashed with saturated sodium bicarbonate, water and brine
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-e3b166cfdb5d4229a52b4fd65b8c0216
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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