Triethylamine → HCID 57513747, compound

HRID 2368422Notes

Reaction equation

HRID 2368422 reaction equation
[NH2:1][C:2]([CH3:25])([CH3:24])[C:3]([NH:5][C:6]1[S:7][C:8]([C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)=[O:4].[CH3:26][C:27]1([C:30](O)=[O:31])[CH2:29][CH2:28]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([C:8]2[S:7][C:6]([NH:5][C:3]([C:2]([NH:1][C:30]([C:27]3([CH3:26])[CH2:29][CH2:28]3)=[O:31])([CH3:25])[CH3:24])=[O:4])=[N:10][C:9]=2[C:11]([F:13])([F:14])[F:12])=[O:23])=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 813261-Methylcyclopropanecarboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57513835HCID 57513835, compound

Product 1

HCID 57513747HCID 57513747, compound

Procedure

A mixture of 2-Amino-N-[5-(4-fluoro-benzoyl)-4-trifluoromethyl-thiazol-2-yl]-2-methyl-propionamide (150 mg, 0.400 mmol), 1-methylcyclopropyl carboxylic acid (80 mg, 0.80 mmol), triethylamine (140 uL, 1.00 mmol) and HBTU (300 mg, 0.809 mmol) was stirred at RT for 18 h, partitioned between ethyl acetate and, sequentially, 3 M HCl and aqueous KOH. The organic extract was dried over MgSO4, concentrated and purified by HPLC to give the title compound. m/z 458.3 (MH+). 1H NMR (CDCl3) δ 7.91 (dd, J=8, 4 Hz, 2H), 7.16 (t, J=8 Hz, 2H), 6.04 (br s, 1H), 1.63 (s, 6H), 1.38 (s, 3H), 1.30-1.25 (m, 2H), 0.70-0.65 (m, 2H), retention time 1.42 min (method A).

Workup

  1. custompartitioned between ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-26a7cdff276648a0b21f9ce46f332595
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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