Triethylamine → HCID 59242738, compound

HRID 2427283Notes

Reaction equation

HRID 2427283 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[C:18]([C:20]1[CH:28]=[CH:27][C:26]2[N:25]([CH2:29][C:30]3[S:34][CH:33]=[N:32][C:31]=3C(O)=O)[C:24]3[CH2:38][C@@H:39]([NH:41][C:42]([O:44][CH:45]([CH3:47])[CH3:46])=[O:43])[CH2:40][C:23]=3[C:22]=2[CH:21]=1)#[N:19].CC[N:50]([CH2:53]C)CC.[CH3:55][Si:56]([CH3:61])([CH3:60])[CH2:57][CH2:58][OH:59]>C1(C)C=CC=CC=1>[CH:45]([O:44][C:42](=[O:43])[NH:41][C@@H:39]1[CH2:38][C:24]2[N:25]([CH2:29][C:30]3[S:34][CH:33]=[N:32][C:31]=3[NH:50][C:53]([O:59][CH2:58][CH2:57][Si:56]([CH3:61])([CH3:60])[CH3:55])=[O:8])[C:26]3[CH:27]=[CH:28][C:20]([C:18]#[N:19])=[CH:21][C:22]=3[C:23]=2[CH2:40]1)([CH3:46])[CH3:47]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 59242731HCID 59242731, compound

Product 1

HCID 59242738HCID 59242738, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Slowly add diphenylphosphorylazide (5.45 g, 4.27 mL, 19.8 mmol) to a refluxing mixture of 5-((S)-7-cyano-2-isopropoxycarbonylamino-2,3-dihydro-1H-cyclopenta[b]indol-4-ylmethyl)-thiazole-4-carboxylic acid (3.82 g, 9.00 mmol), Et3N (2.00 g, 2.76 mL, 19.8 mmol), and 2-(trimethylsilyl)-ethanol (10 mL, 8.25 g, 69.8 mmol) in toluene (270 mL). Continue at reflux for 3 h, then cool to room temperature. Concentrate the reaction mixture to give 14.85 g crude. Purify on silica gel (115 g) using 20-60% EtOAc/hexanes to give 4.06 g (84%) of the product as a yellow solid. LC-ES/MS m/z 562 (M+Na), 538 (M−H), TR=3.1 min.

Workup

  1. temperatureContinue at reflux for 3 h
  2. concentrationConcentrate the reaction mixture
  3. customto give 14.85 g crude
  4. customPurify on silica gel (115 g)

Sources & evidence

ORD record
ord-bf2a2bc0dd3a4af4b2e3224e6abd37ed
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

Loading…