Triethylamine → HCID 71272332, compound

HRID 2175410Notes

Reaction equation

HRID 2175410 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[S:14][C:13]([C:15]([NH2:17])=O)=[N:12][N:11]=2)[CH:5]=[C:4]([O:18][CH2:19][C@H:20]2[CH2:22][C@@H:21]2[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][N:24]=2)[N:3]=1.CCN(CC)CC.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C1COCC1>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[S:14][C:13]([C:15]#[N:17])=[N:12][N:11]=2)[CH:5]=[C:4]([O:18][CH2:19][C@H:20]2[CH2:22][C@@H:21]2[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][N:24]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 71274178HCID 71274178, compound

Product 1

HCID 71272332HCID 71272332, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 5-((2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyrimidin-4-ylamino)methyl)-1,3,4-thiadiazole-2-carboxamide (17-11) (116 mg, 0.15 mmol) in THF was added NEt3 (0.1 mL, 0.7037 mmol) and TFAA (74 mg, 0.35 mmol) at 0° C. The mixture was brought to rt and stirred for 1 h. Then it was concentrated under reduced pressure and purified on silica gel (eluent PE/EA/NEt3=10/1/1%-5/1/1%) to give the product as a pale red solid (40 mg, 70%). 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.38 (dd, J=7.9, 1.7 Hz, 1H), 7.04 (d, J=7.9 Hz, 1H), 5.62 (s, 1H), 5.37 (t, J=5.9 Hz, 1H), 5.05 (d, J=6.2 Hz, 2H), 4.29 (ddd, J=27.7, 11.2, 7.0 Hz, 2H), 2.49 (s, 3H), 2.28 (s, 3H), 2.16-2.03 (m, 1H), 1.96-1.70 (m, 1H), 1.41-1.17 (m, 1H), 1.17-0.94 (m, 1H); LRMS (ESI) calculated M+H for C19H20N7OS: 394.4. Found: 394.1.

Workup

  1. customwas brought to rt
  2. concentrationThen it was concentrated under reduced pressure
  3. custompurified on silica gel (eluent PE/EA/NEt3=10/1/1%-5/1/1%)

Sources & evidence

ORD record
ord-6bff75b1649c463db55333693e6b3e00
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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