HCID 66887603, compound → HCID 67155644, compound

HRID 2196707Notes

Reaction equation

HRID 2196707 reaction equation
IC1C2C(=NC=C(N)C=2)N(S(C2C=CC=CC=2)(=O)=O)C=1.[CH2:21]([O:23][C:24]1[C:32]2[C:27](=[N:28][CH:29]=[C:30]([NH:33][C:34](=[O:50])[C:35]3[C:40]([F:41])=[CH:39][CH:38]=[C:37]([NH:42][S:43]([CH2:46][CH2:47][CH3:48])(=[O:45])=[O:44])[C:36]=3[F:49])[CH:31]=2)[N:26]([S:51]([C:54]2[CH:60]=[CH:59][C:57]([CH3:58])=[CH:56][CH:55]=2)(=[O:53])=[O:52])[CH:25]=1)[CH3:22]>CO>[CH2:21]([O:23][C:24]1[C:32]2[C:27](=[N:28][CH:29]=[C:30]([NH:33][C:34](=[O:50])[C:35]3[C:40]([F:41])=[CH:39][CH:38]=[C:37]([NH:42][S:43]([CH2:46][CH2:47][CH3:48])(=[O:45])=[O:44])[C:36]=3[F:49])[CH:31]=2)[N:26]([S:51]([C:54]2[CH:60]=[CH:59][C:57]([CH3:58])=[CH:56][CH:55]=2)(=[O:52])=[O:53])[CH:25]=1)[CH3:22].[CH2:21]([O:23][C:24]1[C:32]2[C:27](=[N:28][CH:29]=[C:30]([NH:33][C:34](=[O:50])[C:35]3[C:40]([F:41])=[CH:39][CH:38]=[C:37]([NH:42][S:43]([CH2:46][CH2:47][CH3:48])(=[O:45])=[O:44])[C:36]=3[F:49])[CH:31]=2)[NH:26][CH:25]=1)[CH3:22]

Participants

5

Reactant 2

HCID 66887603HCID 66887603, compoundHCID 67155715HCID 67155715, compound

Product 2

HCID 67155644HCID 67155644, compoundYield 30%HCID 67155715HCID 67155715, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(3-Ethoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide was prepared following Example 32, Step D, substituting 3-ethoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-amine for 3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine. N-(3-Ethoxy-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide was then subjected to methanol/aqueous potassium carbonate at 60° C. for 1 hour to give N-(3-ethoxy-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (30%). 1H NMR (400 MHz, d6-DMSO) δ 11.03 (s, 1H), 10.83 (s, 1H), 8.31-8.35 (m, 2H), 7.10-7.54 (m, 2H), 7.05 (s, 1H), 4.00-4.06 (m, 2H), 3.00-3.06 (m, 2H), 1.70-1.76 (m, 2H), 1.36-1.40 (m, 3H), 0.94-1.01 (m, 3H); (APCI-pos) M+1=439.1 (APCI-pos) M+1=439.1.

Sources & evidence

ORD record
ord-1ed676054d1049ed9ad903685624d4ee
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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