Triethylamine → HCID 11848815, compound

HRID 641258Notes

Reaction equation

HRID 641258 reaction equation
[N:1]1([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[O:19]=[C:20]1[N:26]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C@@H:36]([C:47](O)=[O:48])[CH2:37][C:38]3[CH:43]=[C:42]([Br:44])[C:41]([OH:45])=[C:40]([Br:46])[CH:39]=3)=[O:34])[CH2:29][CH2:28]2)[CH2:25][CH2:24][C:23]2[CH:50]=[CH:51][CH:52]=[CH:53][C:22]=2[NH:21]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[O:19]=[C:20]1[N:26]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C@H:36]([CH2:37][C:38]3[CH:39]=[C:40]([Br:46])[C:41]([OH:45])=[C:42]([Br:44])[CH:43]=3)[C:47]([N:10]3[CH2:11][CH2:12][CH:7]([CH:4]4[CH2:5][CH2:6][N:1]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:2][CH2:3]4)[CH2:8][CH2:9]3)=[O:48])=[O:34])[CH2:29][CH2:28]2)[CH2:25][CH2:24][C:23]2[CH:50]=[CH:51][CH:52]=[CH:53][C:22]=2[NH:21]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate2×HCID 22945803Ethyl [4,4′-bipiperidine]-1-acetate2×HCID 67301880(R)-1-carboxy-2-(3,5-dibromo-4-hydroxy-phenyl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 11848815HCID 11848815, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

208 mg (0.82 mmol) ethyl [4,4′]bipiperidinyl-1-yl-acetate were added to a solution of 500 mg (0.82 mmol) of (R)-1-carboxy-2-(3,5-dibromo-4-hydroxy-phenyl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 315 mg (0.98 mmol) TBTU and 150 μL (1.06 mmol) triethylamine in 5 mL DMF and the reaction mixture was stirred overnight at RT. To complete the reaction a further 315 mg (0.98 mmol) TBTU, 150 μL (1.06 mmol) triethylamine and 208 mg (0.82 mmol) ethyl [4,4′]bipiperidinyl-1-yl-acetate were added and the mixture was again stirred overnight at RT. The reaction mixture was purified directly by HPLC without any further working up. The fractions containing the product were combined, evaporated down i.vac., neutralised with saturated NaHCO3 solution, the aqueous phase was extracted twice with 100 mL DCM and the combined organic phases were dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was triturated with DIPE, suction filtered and dried in the air.

Workup

  1. additionwere added
  2. waitthe mixture was again stirred overnight at RT
  3. customThe reaction mixture was purified directly by HPLC without
  4. additionThe fractions containing the product
  5. customevaporated down i.vac
  6. extractionthe aqueous phase was extracted twice with 100 mL DCM
  7. dry with materialthe combined organic phases were dried over Na2SO4
  8. customwas triturated with DIPE, suction
  9. filtrationfiltered
  10. customdried in the air

Sources & evidence

ORD record
ord-037e02abeb8e44cf8b2113bb25f012d9
Source dataset
uspto-grants-2010_04
Patent number
US07696196B2

Reaction notes

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