Dichloromethane → HCID 86642471, compound

HRID 2079825Notes

Reaction equation

HRID 2079825 reaction equation
C(OC([O:8][NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[N:16][C:17]=1[N:18]1[CH2:25][CH:24]2[CH:20]([CH2:21][N:22]([CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)[CH2:23]2)[CH2:19]1)=[O:11])C)C(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>CO>[OH:8][NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[N:16][C:17]=1[N:18]1[CH2:25][CH:24]2[CH:20]([CH2:21][N:22]([CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)[CH2:23]2)[CH2:19]1)=[O:11]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86642470HCID 86642470, compound

Product 1

HCID 86642471HCID 86642471, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-(1-isobutoxyethoxy) 6-(5-naphthalen-2-ylmethyl-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)pyridine-5-carboxamide (0.199 g, 0.4 mmol) was added TFA:DCM:MeOH (8 ml, 1:2:2). The solution was stirred for 6 h and then concentrated under vacuum. The residue was suspended in MeOH and poured into EtOH (250 ml). The mixture was washed with 1:1 saturated sodium bicarbonate/1M NaOH (100 ml), and water (50 ml). The organic fraction was dried (Na2SO4), concentrated and purified by reverse phase HPLC to yield the title compound (9 mg, 5%). m/z 389.25 [M+H]+; 1H NMR (300 MHz, CD3OD) δ: 2.64 (2H, d, J=5.3 Hz), 2.90-3.07 (4H, m), 3.37-3.58 (4H, m), 3.89 (2H, s), 6.46 (1H, d, J=8.9 Hz), 7.33-7.44 (3H, m), 7.70-7.80 (5H, m), 8.37 (1H, d, J=2.2 Hz).

Workup

  1. concentrationconcentrated under vacuum
  2. additionpoured into EtOH (250 ml)
  3. washThe mixture was washed with 1:1 saturated sodium bicarbonate/1M NaOH (100 ml), and water (50 ml)
  4. dry with materialThe organic fraction was dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-90700f0b5d9b4349aea51628ddd065a2
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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