HCID 43390104, compound → HCID 22633902, compound

HRID 2417205Notes

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

Participants

Reactant 2

HCID 43390104HCID 43390104, compound

HCID 69306956HCID 69306956, compound

Product 1

HCID 22633902HCID 22633902, compoundYield 53%

Procedure

The product of Example 2 (0.442 g, 1.37 mmol) was coupled to N-(3-hydroxypropyl)-1-benzofuran-2-carboxamide (0.3 g, 1.37 mmol) using the procedure of Example 3 to provide 0.37 g (53% yield) of an off white powder. MP 184-186° C.; 1H NMR (DMSO-d6): δ 1.9 (s, CH3), 2.04 (t, CH2), 3.16 (s, CH3), 3.46 (q, CH2), 4.0 (t, CH2), 7.01 (d, 2 Ar H) 7.30-7.78 (m, 10 Ar H), 8.56 (t, NH), 12.4 (br s, OH). Electrospray Mass Spec: m/z 523.2 (M+H)+.

Workup

customto provide 0.37 g (53% yield) of an off white powder

Sources & evidence

ORD record: ord-ecd4fa81e6be4f2aac16d6be2eb39b3e
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825352B2

Reaction notes

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