N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine → HCID 57513707, compound

HRID 2368428Notes

Reaction equation

HRID 2368428 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[C:24]([NH2:33])[S:25][C:26]=2[N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:18][CH:17]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]([C:10](=[O:12])[NH:33][C:24]1[S:25][C:26]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)[N:23]=1)([CH3:14])[CH3:13])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57476895HCID 57476895, compound

Product 1

HCID 57513707HCID 57513707, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-tert-Butoxycarbonylamino-2-methyl-propionic acid (1.5 eq) and 4-(4-Fluoro-phenyl)-5-morpholin-4-yl-thiazol-2-ylamine (1 eq)) in DMF (50 mL) were added HATU (1.5 eq) and TEA (2 eq). Reaction was stirred at 60 C over night. Aqueous work up followed by silica gel chromatography afforded the title compound. LCMS Method A Rt=1.51 (M+1=465.1, M−1=463.1). 1H NMR (400 MHz, DMSO-D6) 1.21 (s, 1H) 1.28-1.40 (m, 14H) 2.80-2.87 (m, 4H) 3.70-3.77 (m, 4H) 7.21-7.27 (m, 2H) 8.10-8.16 (m, 2H) 11.59 (s, 1H).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-5649f3910cda43b4915e4da8009e881e
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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