Diisopropylethylamine → HCID 57947909, compound

HRID 409763Notes

Reaction equation

HRID 409763 reaction equation
[Cl:1][C:2]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:3]=1[CH2:4][NH:5][C:6](=[O:31])[N:7]([C@H:9]([CH2:15][O:16][C:17](=[O:30])[NH:18][C:19]1[N:20]=[CH:21][C:22]2[C:27]([CH:28]=1)=[CH:26][C:25]([F:29])=[CH:24][CH:23]=2)[CH2:10][CH2:11][C:12](O)=[O:13])[CH3:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:61]([O:65][C:66]([N:68]1[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]1)=[O:67])([CH3:64])([CH3:63])[CH3:62].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:3]=1[CH2:4][NH:5][C:6](=[O:31])[N:7]([C@H:9]([CH2:15][O:16][C:17](=[O:30])[NH:18][C:19]1[N:20]=[CH:21][C:22]2[C:27]([CH:28]=1)=[CH:26][C:25]([F:29])=[CH:24][CH:23]=2)[CH2:10][CH2:11][C:12]([N:71]1[CH2:72][CH2:73][N:68]([C:66]([O:65][C:61]([CH3:64])([CH3:62])[CH3:63])=[O:67])[CH2:69][CH2:70]1)=[O:13])[CH3:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57947598HCID 57947598, compound

Product 1

HCID 57947909HCID 57947909, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-(6-fluoroisoquinolin-3-ylcarbamoyloxy)pentanoic acid (83 mg, 0.160 mmol, 1.0 equiv) in DMF (1 mL) were added HBTU (72 mg, 0.191 mmol, 1.2 equiv.), tert-butyl-1-piperazine carboxylate (59 mg, 0.320 mmol, 2.0 equiv.) and DIEA (83 μL, 0.480 mmol, 3.0 equiv.). The reaction mixture was stirred 1 h at RT and purified on RP-HPLC using a mixture of acetonitrile and H2O to give (S)-tert-butyl 4-(4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-(6-fluoroisoquinolin-3-ylcarbamoyloxy)pentanoyl)piperazine-1-carboxylate (61 mg, 55%). LRMS (M+H+) m/z 689.3.

Workup

  1. custompurified on RP-HPLC
  2. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-86c34a1554ec4b259df5981ff914d4e0
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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