N-[4-(thiazol-2-yl)benzyl]pyridin-3-ylsulfonamide → tert-Butyl ({6-[(benzofuran-2-ylmethyl)(pyridin-3-ylsulfonyl)aminomethyl]-pyridin-2-yl}tert-butoxycarbonylamino)acetate

HRID 2359785Notes

Reaction equation

HRID 2359785 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11](CO)[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[O:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH:27]=[C:26]1[CH2:34]NS(C1C=NC=CC=1)(=O)=O.S1C=CN=C1C1C=CC([CH2:54][NH:55][S:56]([C:59]2[CH:60]=[N:61][CH:62]=[CH:63][CH:64]=2)(=[O:58])=[O:57])=CC=1>>[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:54]([CH2:34][C:26]2[O:25][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[CH:27]=2)[NH:55][S:56]([C:59]2[CH:60]=[N:61][CH:62]=[CH:63][CH:64]=2)(=[O:58])=[O:57])[N:10]=1)[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 66717376N-[4-(thiazol-2-yl)benzyl]pyridin-3-ylsulfonamideHCID 66717414N-(Benzofuran-2-ylmethyl)pyridin-3-ylsulfonamideHCID 86651768Tert-butyl[tert-butoxycarbonyl(6-hydroxymethylpyridin-2-yl)amino]acetate

Product 1

HCID 86716527tert-Butyl ({6-[(benzofuran-2-ylmethyl)(pyridin-3-ylsulfonyl)aminomethyl]-pyridin-2-yl}tert-butoxycarbonylamino)acetateYield 88%

Procedure

Reaction and post-treatment were carried out in the same manner as in Example 2-(a) except for using tert-butyl[tert-butoxycarbonyl(6-hydroxymethylpyridin-2-yl)amino]acetate (252 mg, 0.745 mmol) obtained in Reference Example 3-(b), and using N-(benzofuran-2-ylmethyl)pyridin-3-ylsulfonamide (215 mg, 0.747 mmol) obtained in Reference Example 10-(c) in place of N-[4-(thiazol-2-yl)benzyl]pyridin-3-ylsulfonamide to afford the title compound (397 mg) as a white foam. (Yield: 88%) Mass spectrum (FAB, m/z): 609 (M++1).

Workup

  1. customReaction
  2. customobtained in Reference Example 3-(b)

Sources & evidence

ORD record
ord-acc0782e1fb14420885420556b7e0ab6
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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