Diisopropylethylamine → HCID 57513812, compound

HRID 2368447Notes

Reaction equation

HRID 2368447 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15]([OH:17])=O.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:26]=[C:27]([NH2:33])[S:28][C:29]=2[CH2:30][CH2:31][CH3:32])=[CH:21][CH:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[N:26]=[C:27]([NH:33][C:15]([C@@H:11]3[CH2:12][CH2:13][CH2:14][N:10]3[C:2]3[O:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[O:17])[S:28][C:29]=2[CH2:30][CH2:31][CH3:32])=[CH:23][CH:24]=1

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 280654204-(4-Fluorophenyl)-5-propyl-1,3-thiazol-2-amine2×HCID 57513846HCID 57513846, compound2×

Product 1

HCID 57513812HCID 57513812, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 70 mg of (S)-1-benzooxazol-2-yl-pyrrolidine-2-carboxylic acid (intermediate 2), 71 mg of 4-(4-fluoro-phenyl)-5-propyl-thiazol-2-ylamine (intermediate 1), 128 mg of HATU and 0.16 mL of DIEA in CH2Cl2 was stirred at room temperature overnight. Solvent was evaporated and crude material was purified by chromatography (C-18, CH3CN/H2O) to provide the title compound. 1H NMR (400 MHz, CHLOROFORM-d) ppm 0.98 (t, J=7.33 Hz, 3H) 1.62-1.81 (m, 2H) 2.03-2.37 (m, 4H) 2.52-2.68 (m, 1H) 2.82 (t, 2H) 3.76 (q, J=8.84 Hz, 1H) 3.92 (br. s., 1H) 4.88 (br. s., 1H) 7.02-7.14 (m, 3H) 7.22 (t, J=7.71 Hz, 1H) 7.32 (d, J=7.96 Hz, 1H) 7.41-7.58 (m, 3H). MS m/z 451.0 (M+H), 449.1 (M−H). HRMS calcd for C24H23FN4O2S=450.15257, found=450.15235. HPLC (0-95% ACN in 20 min using 0.1% TFA on 150 mm Atlantis C18 column) Rt=15.36.

Workup

  1. customSolvent was evaporated
  2. customcrude material was purified by chromatography (C-18, CH3CN/H2O)

Sources & evidence

ORD record
ord-fbcb44f57e404deb83319a1857df3d7c
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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