HCID 13832241, compound → HCID 18414730, compound

HRID 2378352Notes

Reaction equation

HRID 2378352 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][NH:28][C:29]([C:31]1[CH:39]=[CH:38][C:34]2[O:35][CH2:36][O:37][C:33]=2[CH:32]=1)=[O:30]>>[O:35]1[C:34]2[CH:38]=[CH:39][C:31]([C:29]([NH:28][CH2:27][CH2:26][CH2:25][O:24][C:19]3[CH:18]=[CH:17][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:14])=[O:15])=[CH:21][CH:20]=3)=[O:30])=[CH:32][C:33]=2[O:37][CH2:36]1

Participants

3

Reactant 2

HCID 13832241HCID 13832241, compoundHCID 69306956HCID 69306956, compound

Product 1

HCID 18414730HCID 18414730, compoundYield 49%

Procedure

The product of Example 2 (0.30 g, 0.92 mmol) was coupled to N-(3-hydroxypropyl)-1,3-benzodioxole-5-carboxamide, prepared according to Example 20, (0.205 g, 0.92 mmol) using the procedure of Example 3 to provide 0.23 g (49% yield) of yellow solid. MP 120° C.; 1H NMR (DMSO-d6): δ 1.63 (m, CH2) 1.9 (s, CH3), 3.20 (s, CH3), 3.6 (m, CH2), 4.1 (m, CH2), 6.07 (s, CH2), 6.9-7.1 (m, 5 Ar H), 7.3-7.5 (m, 3 Ar H), 7.88-7.94 (m, 2 Ar H), 8.52 (br s, NH). Electrospray Mass Spec: m/z 527.2 (M+H)+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-8d755040c40d4ce9b265114146900b66
Source dataset
uspto-grants-2008_12
Patent number
US07470794B2

Reaction notes

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