Dimethylformamide → HCID 57513717, compound

HRID 2368410Notes

Reaction equation

C(O[C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[O:7])(C)(C)C.[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=N[C:44]2[CH:45]=[CH:46][CH:47]=N[C:43]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:58]N(C=O)C>>[CH:43]1([CH2:58][C:6]([NH:8][C:9]([CH3:13])([CH3:14])[C:10]([NH:33][C:24]2[S:25][C:26]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[C:22]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=3)[N:23]=2)=[O:12])=[O:7])[CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

HCID 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 57513717HCID 57513717, compound

Conditions

Temperature: 60 °C

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. overnight. Aqueous work up followed by silica gel chromatography afforded desired product. LCMS Method 10 Rt=1.51 (M+1=465.1. M−1=463.1). 1H NMR (400 MHz, DMSO-D6) ppm 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

customReaction

Sources & evidence

ORD record: ord-8f262dd5002c40cd837e9c0fd1b17c2b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703761B2

Reaction notes

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