Diisopropylethylamine → HCID 178495706, compound

HRID 1413002Notes

Reaction equation

HRID 1413002 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][N:7](C(OC(C)(C)C)=O)[C@H:6]([C:16]2[NH:17][C:18]([C:21]3[CH:26]=[C:25]4[CH2:27][O:28][C:29]5[CH:47]=[C:46]6[C:32]([CH:33]=[CH:34][C:35]7[N:39]=[C:38]([C@@H:40]8[CH2:44][CH2:43][C@H:42]([CH3:45])[NH:41]8)[NH:37][C:36]=76)=[CH:31][C:30]=5[C:24]4=[CH:23][CH:22]=3)=[CH:19][N:20]=2)[CH2:5]1.[CH3:48][O:49][C@H:50]([CH3:60])[C@H:51]([NH:55][C:56]([O:58][CH3:59])=[O:57])[C:52](O)=[O:53].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:59][O:58][C:56](=[O:57])[NH:55][C@@H:51]([C@H:50]([O:49][CH3:48])[CH3:60])[C:52]([N:41]1[C@@H:42]([CH3:45])[CH2:43][CH2:44][C@H:40]1[C:38]1[NH:37][C:36]2[C:46]3[C:32]([CH:33]=[CH:34][C:35]=2[N:39]=1)=[CH:31][C:30]1[C:24]2[C:25]([CH2:27][O:28][C:29]=1[CH:47]=3)=[CH:26][C:21]([C:18]1[NH:17][C:16]([C@@H:6]3[CH2:5][C@H:4]([CH2:3][O:2][CH3:1])[CH2:8][NH:7]3)=[N:20][CH:19]=1)=[CH:22][CH:23]=2)=[O:53]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59540170(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acidHCID 178495689HCID 178495689, compound

Product 1

HCID 178495706HCID 178495706, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl(2S,4S)-4-(methoxymethyl)-2-(5-{2-[(2S,5S)-5-methylpyrrolidin-2-yl]-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (101 mg, 0.159 mmol), (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid (30 mg, 0.159 mmol), HATU (61 mg, 0.159 mmol) and 2 mL 10% DIPEA in DMF was stirred at room temperature for 1.5 hours. Saturated sodium bicarbonate was added and the product was extracted into dichloromethane, dried over sodium sulphate, filtered and concentrated under reduced pressure. This crude product was treated with 5 mL 1.25N HCl in ethanol at 50° C. for 4 h and then it was concentrated under reduced pressure. Saturated sodium bicarbonate was added and the product was extracted into dichloromethane, dried over sodium sulphate, filtered and concentrated under reduced pressure. (74.6 mg)

Workup

  1. extractionthe product was extracted into dichloromethane
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionThis crude product was treated with 5 mL 1.25N HCl in ethanol at 50° C. for 4 h
  6. concentrationit was concentrated under reduced pressure
  7. additionSaturated sodium bicarbonate was added
  8. extractionthe product was extracted into dichloromethane
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-257ae11e8e224a97af72e338b441c329
Source dataset
uspto-grants-2014_12
Patent number
US08921341B2

Reaction notes

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