Diisopropylethylamine → HCID 178498442, compound

HRID 1713746Notes

Reaction equation

HRID 1713746 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C@H:23]3[CH2:28][CH2:27][C@H:26]([CH2:29][C:30](O)=[O:31])[CH2:25][CH2:24]3)=[CH:19][CH:18]=2)=[O:15])=[N:11][N:10]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH:66]1[CH2:75][CH2:74][CH:69]([C:70]([O:72][CH3:73])=[O:71])[CH2:68][CH2:67]1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([C@H:23]3[CH2:28][CH2:27][C@H:26]([CH2:29][C:30]([N:66]4[CH2:75][CH2:74][CH:69]([C:70]([O:72][CH3:73])=[O:71])[CH2:68][CH2:67]4)=[O:31])[CH2:25][CH2:24]3)=[CH:21][CH:22]=2)=[O:15])=[N:11][N:10]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 424914Methyl isonipecotateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178525547HCID 178525547, compound

Product 1

HCID 178498442HCID 178498442, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (trans-4-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetic acid (Example 112, 300 mg, 0.68 mmol) in DMF (3 mL) was added HATU (286 mg, 0.75 mmol), diisopropylethylamine (0.14 mL, 0.75 mmol) followed by methyl isonipecotate (0.15 mL, 0.75 mmol). The reaction mixture was allowed to stir at ambient temperature overnight. The DMF was evaporated and the residue re-dissolved in DMSO/MeCN/H2O (7:2:1); a suspension formed which was filtered, washed with ether (2×10 mL) and dried to leave the title compound (137 mg). The filtrate was purified on an acidic reverse phase HPLC system eluting 5-95% MeCN 0.2% TFA, isolated 112 mg of the title compound (249 mg, 65%) as a solid; 1H NMR δ 1.07-1.16 (m, 2H), 1.36-1.53 (m, 4H), 1.75-1.88 (m, 7H), 2.24 (d, 2H), 2.41-2.47 (m, 1H), 2.59-2.65 (m, 2H), 3.11 (t, 1H), 3.62 (s, 3H), 3.85 (d, 1H), 4.26 (d, 1H), 7.14-7.34 (m, 5H), 7.68 (d, 2H), 8.04 (t, 1H), 10.75 (s, 1H), 10.93 (s, 1H); MS m/e MH+ 564.

Workup

  1. customThe DMF was evaporated
  2. dissolutionthe residue re-dissolved in DMSO/MeCN/H2O (7:2:1)
  3. customa suspension formed which
  4. filtrationwas filtered
  5. washwashed with ether (2×10 mL)
  6. customdried

Sources & evidence

ORD record
ord-a08e76d9553f44a0b10acab1d3b862a8
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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