(6-Chloro-1-benzothiophen-2-yl)methanol → tert-Butyl (tert-butoxycarbonyl {6-[(6-chlorobenzo[b]thiophen-2-ylmethyl)(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetate

HRID 241255Notes

Reaction equation

HRID 241255 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][NH:16][S:17]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[N:10]=1)([CH3:4])([CH3:3])[CH3:2].S1C=CN=C1C1C=CC(CNS(C2C=NC=CC=2)(=O)=O)=CC=1.[Cl:56][C:57]1[CH:58]=[CH:59][C:60]2[CH:64]=[C:63]([CH2:65]O)[S:62][C:61]=2[CH:67]=1>>[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]([CH:15]([CH2:65][C:63]2[S:62][C:61]3[CH:67]=[C:57]([Cl:56])[CH:58]=[CH:59][C:60]=3[CH:64]=2)[NH:16][S:17]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)(=[O:18])=[O:19])[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 36995598(6-Chloro-1-benzothiophen-2-yl)methanolHCID 66717376N-[4-(thiazol-2-yl)benzyl]pyridin-3-ylsulfonamideHCID 86651773Tert-butyl (tert-butoxycarbonyl{6-[(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetate

Product 1

HCID 86651775tert-Butyl (tert-butoxycarbonyl {6-[(6-chlorobenzo[b]thiophen-2-ylmethyl)(pyridin-3-ylsulfonyl)aminomethyl]pyridin-2-yl}amino)acetateYield 104.5%

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 (100 mg, 0.209 mmol) obtained in Reference Example 12-(d) in place of N-[4-(thiazol-2-yl)benzyl]pyridin-3-ylsulfonamide, and using (6-chlorobenzo[b]thiophen-2-yl)methanol (see WO 99/37304A, 41.5 mg, 0.209 mmol) in place of tert-butyl[tert-butoxycarbonyl(6-hydroxymethylpyridin-2-yl)amino]acetate to afford the title compound (144 mg) substantially quantitatively as a slightly yellow liquid.

Workup

  1. customReaction

Sources & evidence

ORD record
ord-66a151d21a894c7d9d6c8753a5af0f98
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

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