Diisopropylethylamine → HCID 68283608, compound

HRID 1527593Notes

Reaction equation

HRID 1527593 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:11]1[C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[N:13]([CH2:20][C:21]([OH:23])=O)[N:12]=1)(=[O:10])[NH2:9].FC(F)(F)C(O)=O.[Cl:31][C:32]1[C:33]([F:49])=[C:34]([C@H:38]([NH:40][C:41]([C@@H:43]2[CH2:48][C@@H:47]3[C@@H:45]([CH2:46]3)[NH:44]2)=[O:42])[CH3:39])[CH:35]=[CH:36][CH:37]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:31][C:32]1[C:33]([F:49])=[C:34]([C@H:38]([NH:40][C:41]([C@@H:43]2[CH2:48][C@@H:47]3[C@@H:45]([CH2:46]3)[N:44]2[C:21](=[O:23])[CH2:20][N:13]2[C:14]3=[CH:15][N:16]=[CH:17][CH:18]=[C:19]3[C:11]([C:8]([NH2:9])=[O:10])=[N:12]2)=[O:42])[CH3:39])[CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68283113HCID 68283113, compoundHCID 86673877HCID 86673877, compound

Product 1

HCID 68283608HCID 68283608, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-carbamoyl-pyrazolo[3,4-c]pyridin-1-yl)-acetic acid trifluoroacetate salt (2.65 g, 7.94 mmol, prepared as described in Scheme A26) in DMF (30 mL) were added successively (1R,3S,5R)-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid, [(R)-1-(3-chloro-2-fluoro-phenyl)-ethyl]-amide trifluoroacetate salt (3.00 g, 7.56 mmol), HBTU (3.44 g, 9.07 mmol) and DIPEA (5.28 mL, 30.2 mmol). The reaction mixture was stirred at RT for 16 h and then was concentrated under vacuum. The residual oil was partitioned between CH2Cl2 and a sat. aq. NaHCO3 solution. A solid precipitated from the resulting emulsion and was filtered off, washed with water and dried under vacuum. The solid was suspended in a mixture of water (150 mL) and MeOH (3 mL), stirred for 1 h at RT, filtered, washed with water and finally dried under vacuum to give the title material as a white powder. MS (LC/MS): 485 [M+H]+; tR (HPLC conditions c): 3.54 min.

Workup

  1. concentrationwas concentrated under vacuum
  2. customThe residual oil was partitioned between CH2Cl2
  3. customA solid precipitated from the resulting emulsion
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried under vacuum
  7. additionThe solid was suspended in a mixture of water (150 mL) and MeOH (3 mL)
  8. stirringstirred for 1 h at RT
  9. filtrationfiltered
  10. washwashed with water
  11. customfinally dried under vacuum

Sources & evidence

ORD record
ord-e7fdecea3ba040fd92742e3df126da58
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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