Diisopropylethylamine → HCID 57463495, compound

HRID 1171968Notes

Reaction equation

HRID 1171968 reaction equation
C([C@@:3]1([CH:10]=[CH2:11])[CH2:5][C@@:4]1([C:7]([O-:9])=[O:8])[NH2:6])C.[C:12]([O:16][C:17]([N:19]1[CH:28]([C:29]([OH:31])=O)[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=3)[CH:25]=2)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CN(C(ON1N=N[C:50]2C=CC=N[C:49]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:49]([O:9][C:7]([C@@:4]1([NH:6][C:29]([CH:28]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:32][C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=4)[CH:25]=3)[CH2:20][N:19]2[C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])=[O:31])[CH2:5][C@H:3]1[CH:10]=[CH2:11])=[O:8])[CH3:50]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59554296HCID 59554296, compoundHCID 86611243HCID 86611243, compound

Product 1

HCID 57463495HCID 57463495, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a flask charged with ethyl-(1R,2S)-1-amino-2-vinylcyclopropyl carboxylate (1, 1.0 g, 5.2 mmol), 2-(tert-butoxycarbonyl)-6-(3-chlorophenoxy)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (2.31 g, 1.1 equiv), and HATU (2.7 g, 1.1 equiv) were added 30 mL DMF to make a solution. It was cooled to 0° C. in an ice-water bath, followed by slow addition of a solution of DIEA (4.4 mL, 4 equiv) in DMF (15 mL) while stirring. The reaction was allowed to warm up to rt and stirred overnight.

Workup

  1. temperatureto warm up to rt
  2. stirringstirred overnight

Sources & evidence

ORD record
ord-b7371775533c4c33b2acd17333ac4847
Source dataset
uspto-grants-2010_11
Patent number
US07829665B2

Reaction notes

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