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Diisopropylethylamine → 4-(2,3-dihydro-1,3-dioxo-1H-pyrrolo[3,4-c]pyridin-2-yl)-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine

HRID 393437
Notes
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Reaction equation

HRID 393437 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C@@H:7]([C:25]([OH:27])=[O:26])[NH:8][C:9]([C:11]2([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[N:39]1[CH:44]=[CH:43][C:42]2[C:45]([O:47][C:48](=O)[C:41]=2[CH:40]=1)=[O:46].C(C1NC=CN=1)(C1NC=CN=1)=O>ClCCl>[O:46]=[C:45]1[C:42]2[CH:43]=[CH:44][N:39]=[CH:40][C:41]=2[C:48](=[O:47])[N:1]1[C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]([C:25]([OH:27])=[O:26])[NH:8][C:9]([C:11]2([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:28][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2783981H,3H-furo(3,4-c)pyridine-1,3-dioneHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 540857504-amino-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine

Product 1

HCID 541291594-(2,3-dihydro-1,3-dioxo-1H-pyrrolo[3,4-c]pyridin-2-yl)-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine
Yield 23.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-amino-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine (98 mg, 0.23 mmol), DIPEA (30 μL, 0.23 mmol) and 3,4-pyridinedicarboxylic acid anhydride (114 mg, 0.77 mmol) in dichloromethane (10 mL) was stirred 18 hr at room temperature. The mixture was concentrated to remove most of the dichloromethane and the residue was taken up in DMF (3 mL). Carbonyl diimidazole (103 mg, 0.64 mmol) was added to the resulting solution and the reaction was allowed to proceed for 18 hr. The resulting mixture was purified directly by RP-HPLC on a 4×30 cm Rainin C-18 column using a gradient of 5 to 95% acetonitrile:water containing 0.75% trifluoroacetic acid at a flow of 49 mL/min over 35 min. The peak eluting at 45.6% acetonitrile was concentrated and lyophilized to give 4-(2,3-dihydro-1,3-dioxo-1H-pyrrolo[3,4-c]pyridin-2-yl)-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine (28 mg) HR FABMS: obs. mass 528.2146. Calcd. mass 528.2134 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove most of the dichloromethane
  3. customThe resulting mixture was purified directly by RP-HPLC on a 4×30 cm Rainin C-18 column
  4. waitwater containing 0.75% trifluoroacetic acid at a flow of 49 mL/min over 35 min
  5. washThe peak eluting at 45.6% acetonitrile
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-70e492292fa24a72b88fb47d81828c98
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06806365B2

Reaction notes

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