Ethyl Acetoacetate → (Z)-6-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(1-hydroxyethylidene)hexanoic acid

HRID 2190200Notes

Reaction equation

HRID 2190200 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]3[C:29]([C:30](=[O:33])[NH:31][CH3:32])=[C:28]([C:34]4[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=4)[O:27][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH:19](S(C)(=O)=O)[C:20]([OH:22])=[O:21])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:3][CH2:2]1.[O:41]=[C:42](C)[CH2:43]C(OCC)=O.BrCCCCN(C1N=C2OC(C3C=CC(C)=CC=3)=C(C(NC)=O)C2=CC=1C1CC1)S(C)(=O)=O>>[CH:1]1([C:4]2[CH:5]=[C:6]3[C:29]([C:30](=[O:33])[NH:31][CH3:32])=[C:28]([C:34]4[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=4)[O:27][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][CH2:18]/[C:19](=[C:42](/[OH:41])\[CH3:43])/[C:20]([OH:22])=[O:21])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 545758766-(N-(4-bromobutyl)methylsulfonamido)-5-cyclopropyl-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamideHCID 580525536-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(methylsulfonyl)hexanoic acid

Product 1

HCID 58052471(Z)-6-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(1-hydroxyethylidene)hexanoic acid

Procedure

Prepared similarly to Example 46 6-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(methylsulfonyl)hexanoic acid, by using ethyl 3-oxobutanoate in the alkylation with 6-(N-(4-bromobutyl)methylsulfonamido)-5-cyclopropyl-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide, followed by hydrolysis.

Workup

  1. customfollowed by hydrolysis

Sources & evidence

ORD record
ord-873dca5fa48547718fed0011a3216158
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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