HCID 136124671, compound → HCID 136124682, compound

HRID 1916247Notes

Reaction equation

HRID 1916247 reaction equation
[CH3:1][S:2]([O:5][C@H:6]([C:8]1[NH:9][C:10](=[O:23])[C:11]2[CH:16]=[N:15][N:14]([CH:17]3[CH2:22][CH2:21]OC[CH2:18]3)[C:12]=2[N:13]=1)[CH3:7])(=[O:4])=[O:3].O[C@H](C1NC(=O)C2C=NN(C3CCOCC3)C=2N=1)C>>[CH3:1][S:2]([O:5][C@H:6]([C:8]1[NH:9][C:10](=[O:23])[C:11]2[CH:16]=[N:15][N:14]([CH:17]3[CH2:22][CH2:21][CH2:18]3)[C:12]=2[N:13]=1)[CH3:7])(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 136124671HCID 136124671, compoundHCID 136124688HCID 136124688, compound

Product 1

HCID 136124682HCID 136124682, compound

Procedure

Compound C18 was prepared according to the general procedure for the synthesis of C5 in Example 1, except that C17 was used in place of C4, and the chromatographic purification was carried out with 0.5% to 1% MeOH in chloroform, rather than 0% to 5% MeOH in dichloromethane, to provide C18 as a solid. Yield: 6.0 g, 19.2 mmol, 79%. LCMS m/z 311.4 (M−1). 1H NMR (400 MHz, CDCl3) 1.85 (d, J=6.6 Hz, 3H), 1.93 (m, 2H), 2.46 (m, 2H), 2.78 (m, 2H), 3.23 (s, 3H), 5.29 (m, 1H), 5.69 (q, J=6.6 Hz, 1H), 8.08 (s, 1H), 11.65 (br s, 1H). 13C NMR (100 MHz, CDCl3) δ 14.93, 20.39, 29.84, 38.75, 51.07, 74.91, 104.98, 134.71, 151.07, 155.61, 159.27.

Workup

  1. customCompound C18 was prepared
  2. customthe chromatographic purification
  3. customto provide C18 as a solid

Sources & evidence

ORD record
ord-861a9d8fe07142a6824318864b31dd9a
Source dataset
uspto-grants-2013_12
Patent number
US08618117B2

Reaction notes

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