1,3-Bis(diphenylphosphino)propane → HCID 25008813, compound

HRID 2116692Notes

Reaction equation

HRID 2116692 reaction equation
[NH2:1][C:2]1[C:45]([C:46]#[CH:47])=[CH:44][C:5]([CH2:6][C@@H:7]([NH:23][C:24]([N:26]2[CH2:31][CH2:30][CH:29]([N:32]3[CH2:38][CH2:37][C:36]4[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=4[NH:34][C:33]3=[O:43])[CH2:28][CH2:27]2)=[O:25])[C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[Cl:48].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[NH2:1][C:2]1[C:45]([CH2:46][CH3:47])=[CH:44][C:5]([CH2:6][C@@H:7]([NH:23][C:24]([N:26]2[CH2:27][CH2:28][CH:29]([N:32]3[CH2:38][CH2:37][C:36]4[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=4[NH:34][C:33]3=[O:43])[CH2:30][CH2:31]2)=[O:25])[C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[Cl:48]

Participants

4

Reactant 2

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 11513116HCID 11513116, compound

Product 1

HCID 25008813HCID 25008813, compound

Reagents, catalysts & solvents 1

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-Catalyst

Procedure

54 mg (73.0 mmol) 4-(2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidine-1-carboxylic acid-{(R)-1-(4-amino-3-chloro-5-ethynyl-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl}-amide, 10 mg (0.02 mmol) of bis(1,5-cyclooctadiene)-di-rhodium(I)-dichloride, 16.5 mg (0.04 mmol) 1,3-bis(diphenylphosphino)-propane were dissolved in 10 ml degassed methanol and 0.1 ml degassed triethylamine and then hydrogenated for 2 hours at ambient temperature and 3 bar hydrogen pressure. The reaction mixture was evaporated down under reduced pressure and taken up in ethyl acetate. The insoluble precipitate was removed by suction filtering and the filtrate was evaporated down under reduced pressure. The residue was purified by column chromatography.

Workup

  1. customdegassed methanol and 0.1 ml
  2. customdegassed triethylamine
  3. customThe reaction mixture was evaporated down under reduced pressure
  4. customThe insoluble precipitate was removed by suction
  5. filtrationfiltering
  6. customthe filtrate was evaporated down under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9cbe570f575046beabec0a21b4adfd22
Source dataset
uspto-grants-2008_10
Patent number
US07439237B2

Reaction notes

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