4-(Aminomethyl)-3-chlorobenzonitrile → HCID 10617537, compound

HRID 1956709Notes

Reaction equation

HRID 1956709 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].C([O:14][C:15]1[C:16](=[O:27])[C:17](=O)[C:18]=1[NH:19][C@H:20]([CH3:25])[C:21]([CH3:24])([CH3:23])[CH3:22])C>C(O)C.C(OCC)C>[Cl:1][C:2]1[CH:9]=[C:8]([CH:7]=[CH:6][C:3]=1[CH2:4][NH:5][C:17]1[C:16](=[O:27])[C:15](=[O:14])[C:18]=1[NH:19][C@H:20]([CH3:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:10]#[N:11]

Participants

5

Reactant 2

HCID 40897884-(Aminomethyl)-3-chlorobenzonitrileHCID 54525291HCID 54525291, compound

Product 1

HCID 10617537HCID 10617537, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2-Chloro-4-cyano-benzylamine (0.30 g, 1.80 mmol, Example 2, Step 3) and (R)-3-ethoxy-4-(1,2,2-trimethyl-propylamino)-cyclobut-3-ene-1,2-dione (0.406 g, 1.80 mmol) were stirred in ethanol (10 mL) at 70° C. for 18 hours. The reaction was cooled and diluted with diethyl ether. Filtration afforded 0.49 g (79%) of (R)-3-chloro-4-{[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-methyl]-benzonitrile which was collected as a white solid: mp 237°-241° C.; [α]25D =+27.30° (10.99 mg/mL, DMSO); 1H NMR (DMSO-d6) δ8.10 (d, 1H), 7.89 (dd, 1H), 7.68 (m, 1H), 7.69 (d, 1H), 7.36 (br d, 1H), 4.87 (m, 2H), 3.90 (m, 1H), 1.12 (d, 3H), 0.86 (s, 9H) ppm. IR (KBr): 3100, 2950, 2250, 1800 cm-1. MS (m/z) 345/347 (M+).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationFiltration

Sources & evidence

ORD record
ord-3d3426ae37c347d6a15ab117073974e6
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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