5-[[(2S)-2-(Acetyloxy)-1-oxopropyl]amino]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide → HCID 136124681, compound

HRID 1916246Notes

Reaction equation

HRID 1916246 reaction equation
[OH:1][C@H:2]([C:4]1[NH:5][C:6](=[O:19])[C:7]2[CH:12]=[N:11][N:10]([CH:13]3[CH2:18][CH2:17]OC[CH2:14]3)[C:8]=2[N:9]=1)[CH3:3].C(O[C@@H](C)C(NC1N(C2CCOCC2)N=CC=1C(=O)N)=O)(=O)C>>[CH:13]1([N:10]2[C:8]3[N:9]=[C:4]([C@@H:2]([OH:1])[CH3:3])[NH:5][C:6](=[O:19])[C:7]=3[CH:12]=[N:11]2)[CH2:14][CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 594183275-[[(2S)-2-(Acetyloxy)-1-oxopropyl]amino]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamideHCID 136124688HCID 136124688, compound

Product 1

HCID 136124681HCID 136124681, compound

Procedure

Compound C17 was prepared according to the general procedure for the synthesis of C4 in Example 1, except that C16 was used in place of C3. Additionally, in this case the crude product was purified via silica gel chromatography (Eluant: 50:1 chloroform:MeOH), to afford C17 as a solid. Yield 5.70 g, 24.3 mmol, 87%. LCMS m/z 235.3 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.64 (d, J=6.6 Hz, 3H), 1.91 (m, 2H), 2.44 (m, 2H), 2.75 (m, 2H), 4.26 (br s, 1H), 4.89 (q, J=6.6 Hz, 1H), 5.25 (m, 1H), 8.06 (s, 1H), 11.07 (br s, 1H). 13C NMR (100 MHz, CDCl3) δ 14.93, 22.42, 29.84, 50.92, 67.67, 104.42, 134.66, 151.71, 159.25, 161.48.

Workup

  1. customCompound C17 was prepared
  2. customAdditionally, in this case the crude product was purified via silica gel chromatography (Eluant: 50:1 chloroform:MeOH)
  3. customto afford C17 as a solid

Sources & evidence

ORD record
ord-e2ddcaff04054057973b970af0c85357
Source dataset
uspto-grants-2013_12
Patent number
US08618117B2

Reaction notes

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