Triethylamine → HCID 16734598, compound

HRID 1864629Notes

Reaction equation

HRID 1864629 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:37][C:38]3[CH:47]=[C:46]([CH3:48])[C:41]4[NH:42][C:43](=[O:45])[O:44][C:40]=4[CH:39]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([CH:27]4[CH2:32][CH2:31][N:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:49]=[CH:50][CH:51]=[CH:52][C:4]=2[NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[N:82]1([CH2:88][CH2:89]O)[CH2:87][CH2:86][O:85][CH2:84][CH2:83]1>CN(C=O)C.C(O)=O>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:37][C:38]3[CH:47]=[C:46]([CH3:48])[C:41]4[NH:42][C:43](=[O:45])[O:44][C:40]=4[CH:39]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([CH:27]4[CH2:32][CH2:31][N:30]([CH2:33][C:34]([O:36][CH2:89][CH2:88][N:82]5[CH2:87][CH2:86][O:85][CH2:84][CH2:83]5)=[O:35])[CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:49]=[CH:50][CH:51]=[CH:52][C:4]=2[NH:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 611632-MorpholinoethanolHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59258281HCID 59258281, compound

Product 1

HCID 16734598HCID 16734598, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 90 mg (0.13 mmol) (R)-2-(1′-carboxymethyl-4,4′-bipiperidinyl-1-yl)-1-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-ylmethyl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 48 mg (0.15 mmol) TBTU and 26 μL (0.19 mmol) triethylamine in 1.4 mL DMF was stirred for 1 h at RT. Then 18 μL (0.15 mmol) 2-morpholin-4-yl-ethanol was added. The reaction mixture was stirred for 16 h at RT. 4 drops of formic acid were added, the mixture was filtered through a syringe filter and purified by HPLC. The fractions containing the product were combined, made alkaline with 5% NaHCO3 solution, extracted with 50 mL EtOAc and the organic phase was dried on Na2SO4. After the desiccant and solvent had been eliminated the residue was triturated with DIPE, suction filtered and dried.

Workup

  1. filtrationthe mixture was filtered through a syringe
  2. filtrationfilter
  3. custompurified by HPLC
  4. additionThe fractions containing the product
  5. extractionextracted with 50 mL EtOAc
  6. customthe organic phase was dried on Na2SO4
  7. customwas triturated with DIPE, suction
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-ee449c4e99bd41d092ba35c628122b63
Source dataset
uspto-grants-2009_12
Patent number
US07625886B2

Reaction notes

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