Ammonia → HCID 16046384, compound

HRID 1297523Notes

Reaction equation

HRID 1297523 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1Br)[CH:18]([NH:23][C:24]1[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:26][CH:25]=1)[CH2:17][CH2:16]2)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37]([Cu])#[N:38].N>CN1C(=O)CCC1>[CH2:1]([O:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[C:37]#[N:38])[CH:18]([NH:23][C:24]1[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:26][CH:25]=1)[CH2:17][CH2:16]2)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 58915023tert-butyl 4-[N-(5-(2-benzyloxyethanoylamino)-6-bromoindan-1-yl)amino]benzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 16046384HCID 16046384, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of tert-butyl 4-[N-(5-(2-benzyloxyethanoylamino)-6-bromoindan-1-yl)amino]benzoate (0.210 g, 0.38 mmol) in anhydrous NMP (2.2 ml) was added CuCN (0.068 g, 0.76 mmol). The reaction flask was placed in an oil bath preheated to 150° C. and it was stirred at this temperature for 3 h under argon. The mixture was then allowed to cool to room temperature and poured into a mixture of liquid ammonia (d=0.88, 2 ml) and ice-water (5 ml). This mixture was stirred at room temperature for 5 min, the brown precipitate was then collected by filtration and washed with water. This precipitate was then suspended in CH2Cl2 (70 ml), dried (Na2SO4), and concentrated in vacuo. Purification of the residue by column chromatography, on elution with 35% AcOEt in hexane, afforded a brown solid (0.084 g, 45%); mp 194-195° C.; 1H-NMR (250 MHz, CDCl3, TMS) 1.55 (s, 9H, C(CH3)3), 1.95, 2.64 (2×m, 1H each, 2-CH2 indanyl), 2.99 (m, 2H, 3-CH2 indanyl), 4.13, 4.72 (2×s, 2H each, PhCH2 and OCH2CO), 4.22 (d, J=8.1 Hz, 1H, N10—H), 5.05 (m, 1H, 1-CH indanyl), 6.65 (d, J=8.7 Hz, 2H, 3,5-ArH), 7.39 (m, 5H, PhCH2), 7.54, 8.37 (2×s, 1H each, 4-H and 7-H), 7.86 (d, J=8.7 Hz, 2H, 2,6-ArH), 9.06 (s, 1H, CONH); MS (ESI, m/z) 520 {(M+Na)+, 100%,}; Found: C, 72.26; H, 6.26; N, 8.41; C30H31N3O4 requires C, 72.41; H, 6.28; N, 8.44%.

Workup

  1. customThe reaction flask was placed in an oil bath
  2. custompreheated to 150° C.
  3. stirringThis mixture was stirred at room temperature for 5 min
  4. filtrationthe brown precipitate was then collected by filtration
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by column chromatography
  9. washon elution with 35% AcOEt in hexane

Sources & evidence

ORD record
ord-d5bfb8490a1046b28ccc2164849868c8
Source dataset
uspto-grants-2007_07
Patent number
US07250511B2

Reaction notes

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