Aminoacetaldehyde dimethyl acetal → HCID 24991638, compound

HRID 388540Notes

Reaction equation

HRID 388540 reaction equation
[CH2:1]([N:8]1[CH2:26][CH2:25][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:14](=[O:23])[CH2:13][C:12]2=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:29](OC)[CH2:30][NH2:31]>CO>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2([C:12]3[NH:31][CH:30]=[CH:29][C:13]=3[C:14](=[O:23])[N:15]2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[CH2:25][CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 59252699HCID 59252699, compound

Product 1

HCID 24991638HCID 24991638, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 8-benzyl-1-(3-fluorophenyl)-1,8-diazaspiro[4.5]decane-2,4-dione (Intermediate 1A.4-1, 100 mg, 0.29 mmol) in methanol (0.1 ml) was added 2,2-dimethoxyethylamine (2 ml). The reaction was allowed to stir at 100° C. until the starting material was consumed. The reaction was concentrated in vacuo, and the residue was dissolved in toluene. The reaction was treated with a catalytic amount of p-toluenesulfonic acid and allowed to stir at 110° C. for 18 h. The crude reaction was purified via reverse phase chromatography to yield 1-benzyl-5′-(3-fluorophenyl)-1′H-spiro[piperidine-4,6′-pyrrolo[3,4-b]pyrrol]-4′(5′H)-one. LCMS (M+H) 376.1. 1H NMR (400 MHz, CD3OD) δ 7.50 (m, 7H), 7.23 (td, J=8.4, 2.1 Hz, 2H), 7.07 (m, 3H), 6.43 (d, J=2.8 Hz, 1H), 4.41 (s, 2H), 3.64 (d, J=13.6 Hz, 2H), 3.43 (t, J=12.6 Hz, 3H), 2.28 (td, J=14.1, 4.0 Hz, 2H), 2.02 (d, J=15.6 Hz, 2H).

Workup

  1. customwas consumed
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutionthe residue was dissolved in toluene
  4. additionThe reaction was treated with a catalytic amount of p-toluenesulfonic acid
  5. stirringto stir at 110° C. for 18 h
  6. customThe crude reaction
  7. customwas purified via reverse phase chromatography

Sources & evidence

ORD record
ord-43ea9e2a0d4c49be89bd5416ee434682
Source dataset
uspto-grants-2013_02
Patent number
US08377954B2

Reaction notes

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