Water → HCID 15952177, compound

HRID 2244244Notes

Reaction equation

HRID 2244244 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][N:22]3[C:30]([C:33]([NH:35][CH2:36][C:37]4[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=4)=[O:34])=[CH:31][CH:32]=[C:21]3[CH2:20]2)=[O:18])=[CH:13][CH:12]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][N:22]3[C:30]([C:33]([NH:35][CH2:36][C:37]4[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=4)=[O:34])=[CH:31][CH:32]=[C:21]3[CH2:20]2)=[O:18])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86609691HCID 86609691, compound

Product 1

HCID 15952177HCID 15952177, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10-{[2′-(azidomethyl)-1,1′-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide (0.49 mmole) of Step B in tetrahydrofuran (3 mL) was added solid triphenylphosphine (0.55 mmole). The mixture was stirred at room temperature for 16 hours. Water (0.3 mL) was then added and the reaction mixture was heated to 45° C. for 3 hours. The solvent was removed by evaporation and the residue was extracted with dichloromethane. The organic solution was dried over anhydrous sodium sulfate, and evaporated. The residue was purified by HPLC (normal phase, 20-70% gradient of [20% methanol in dichloromethane] and hexane, Luna CN bonded packing) and crystallized upon solvent evaporation, m.p. 115-120° C.

Workup

  1. temperaturethe reaction mixture was heated to 45° C. for 3 hours
  2. customThe solvent was removed by evaporation
  3. extractionthe residue was extracted with dichloromethane
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by HPLC (normal phase, 20-70% gradient of [20% methanol in dichloromethane] and hexane, Luna CN bonded packing)
  7. customcrystallized upon solvent evaporation, m.p. 115-120° C.

Sources & evidence

ORD record
ord-be3334d47a7549f888a6cc2e28b5b363
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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