HCID 22633904, compound → HCID 69311389, compound

HRID 2378353Notes

Reaction equation

HRID 2378353 reaction equation
C[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N:11]([S:13]([C:16]2[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH3:12])[C:3]=1[CH3:23].[OH:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([C:32]1[CH:40]=[CH:39][C:35]2[O:36][CH2:37][O:38][C:34]=2[CH:33]=1)=[O:31]>>[O:36]1[C:35]2[CH:39]=[CH:40][C:32]([C:30]([NH:29][CH2:28][CH2:27][CH2:26][CH2:25][O:24][C:19]3[CH:20]=[CH:21][C:16]([S:13]([N:11]([CH3:12])[C:4]4[C:3]([CH3:23])=[CH:2][CH:10]=[CH:9][C:5]=4[C:6]([OH:8])=[O:7])(=[O:15])=[O:14])=[CH:17][CH:18]=3)=[O:31])=[CH:33][C:34]=2[O:38][CH2:37]1

Participants

3

Reactant 2

HCID 22633904HCID 22633904, compoundHCID 69306956HCID 69306956, compound

Product 1

HCID 69311389HCID 69311389, compoundYield 60%

Procedure

The product of Example 2 (0.30 g, 0.92 mmol) was coupled to N-(4-hydroxybutyl)-1,3-benzodioxole-5-carboxamide, prepared according to Example 21, (0.23 g, 0.96 mmol) using the procedure of Example 3 to provide 0.30 g (60% yield) of yellow solid. MP 110° C.; 1H NMR (DMSO-d6): δ 1.66-1.80 (m,CH2, CH2)1.89 (s, CH3), 3.1 (s, CH3), 3.39-3.45 (m, CH2), 4.08 (t, CH2), 6.08 (s, CH2), 6.9 (d, 1 Ar H), 7.04-7.08 (m, 2 Ar H), 7.33-7.45 (m, 5 Ar H), 7.53-7.58 (m, 2 Ar H), 8.39 (t, NH), 12.8 (s, OH). Electrospray Mass Spec: m/z 541.2 (M+H)+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-03413bbe54034010986804786a3e8ff2
Source dataset
uspto-grants-2008_12
Patent number
US07470794B2

Reaction notes

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