N-[4-(thiazol-2-yl)benzyl]pyridin-3-ylsulfonamide → Tert-butyl[tert-butoxycarbonyl(6-hydroxymethylpyridin-2-yl)amino]acetate

HRID 241257Notes

Reaction equation

HRID 241257 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][N:8]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]NS(C2C=NC=CC=2)(=O)=O)[N:10]=1)([CH3:4])([CH3:3])[CH3:2].S1C=CN=C1C1C=CC(CNS(C2C=NC=CC=2)(=O)=[O:46])=CC=1.N1C=CC(C2C=CC(CO)=CC=2)=CN=1>>[C:1]([O:5][C:6](=[O:33])[CH2:7][N:8]([C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][OH:46])[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 66717376N-[4-(thiazol-2-yl)benzyl]pyridin-3-ylsulfonamideHCID 667174174-(Pyridazin-4-yl)benzyl alcoholHCID 86651773Tert-butyl (tert-butoxycarbonyl{6-[(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetate

Product 1

HCID 86651768Tert-butyl[tert-butoxycarbonyl(6-hydroxymethylpyridin-2-yl)amino]acetate

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-[(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetate (158 mg, 0.330 mmol) obtained in Reference Example 12-(d) in place of N-[4-(thiazol-2-yl)benzyl]pyridin-3-ylsulfonamide, and using 4-(pyridazin-4-yl)benzyl alcohol (60.2 mg, 0.323 mmol) obtained in Reference Example 13 in place of tert-butyl[tert-butoxycarbonyl(6-hydroxymethylpyridin-2-yl)amino]acetate to afford the title compound (152 mg) as a white foam. (Yield: 73%)

Workup

  1. customReaction

Sources & evidence

ORD record
ord-5dce84a0f3cf437490e5f4b2fb6e336b
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

Loading…