Dimethylformamide → HCID 86642470, compound

HRID 2079824Notes

Reaction equation

HRID 2079824 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[CH2:16][CH:15]2[CH2:17][N:18]([C:20]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26](O)=[O:27])[CH2:19][CH:14]2[CH2:13]1.C1C=CC2[N:37]([OH:38])N=NC=2C=1.CCN=C=N[CH2:44][CH2:45][CH2:46]N(C)C.Cl.CCN([CH:57]([CH3:59])C)C(C)C.CN([CH:63]=[O:64])C>CCOCC>[CH2:63]([O:64][CH:57]([O:38][NH:37][C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[N:25][C:20]=1[N:18]1[CH2:17][CH:15]2[CH:14]([CH2:13][N:12]([CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[CH2:16]2)[CH2:19]1)=[O:27])[CH3:59])[CH:45]([CH3:44])[CH3:46]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 668762166-(5-Naphthalen-2-ylmethyl-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)pyridine-5-carboxylic acid

Product 1

HCID 86642470HCID 86642470, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6-(5-naphthalen-2-ylmethyl-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)pyridine-5-carboxylic acid (0.24 g, 0.6 mmol) in DMF (5 ml) were added HOBt (0.26 g, 1.7 mmol), EDCl (0.303 g, 1.6 mmol), DIPEA (1 ml, 5.8 mmol), and intermediate D (1 ml, 7.4 mmol). The mixture was stirred overnight and then poured into Et2O (250 ml). This was washed with water (50 ml), saturated sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml). The extract was then dried (MgSO4), concentrated and purified by flash column chromatography (4% MeOH-DCM) to yield the title compound (0.199 g, 58%). 1H NMR (300 MHz, d6-DMSO) δ: 11.17 (1H, br s), 8.50 (1H, d, J=2.1 Hz), 7.81-7.90 (4H, m), 7.77 (1H, s), 7.42-7.50 (3H, m), 6.52 (1H, d, J=8.8 Hz), 4.95 (2H, q, J=7.0 Hz), 3.61-3.74 (6H, m), 2.88-2.99 (2H, m), 2.60-2.69 (2H, m), 1.72-1.84 (1H, m), 1.31 (3H, d, J=5.1 Hz), 0.86 (6H, d, J=6.6 Hz).

Workup

  1. washThis was washed with water (50 ml), saturated sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml)
  2. dry with materialThe extract was then dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (4% MeOH-DCM)

Sources & evidence

ORD record
ord-134d08ea29064572b22e2664eb501b05
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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