Tert-butyl [tert-butoxycarbonyl(6-{[4-(pyrazol-1-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-yl)amino}acetate → (6-{(Pyridin-2-ylsulfonyl)[4-(4-trifluoromethylthiazol-2-yl)benzyl]aminomethyl}pyridin-2-ylamino)acetic acid

HRID 241267Notes

Reaction equation

HRID 241267 reaction equation
C([O:5][C:6](=[O:49])[CH2:7][N:8](C(OC(C)(C)C)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)(=[O:35])=[O:34])[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[S:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=3)=[CH:20][CH:19]=2)[N:10]=1)(C)(C)C.C(OC(=O)CN(C(OC(C)(C)C)=O)C1C=CC=C(C(CC2C=CC(N3C=CC=N3)=CC=2)NS(C2C=CC=CN=2)(=O)=O)N=1)(C)(C)C>>[N:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[S:33]([CH:15]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:25][CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[N:28]=2)=[CH:20][CH:19]=1)[C:11]1[N:10]=[C:9]([NH:8][CH2:7][C:6]([OH:49])=[O:5])[CH:14]=[CH:13][CH:12]=1)(=[O:34])=[O:35]

Participants

3

Reactant 2

HCID 86651782Tert-butyl [tert-butoxycarbonyl(6-{[4-(pyrazol-1-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-yl)amino}acetateHCID 86651785Tert-butyl[tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(4-trifluoromethylthiazol-2-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate

Product 1

HCID 66717235(6-{(Pyridin-2-ylsulfonyl)[4-(4-trifluoromethylthiazol-2-yl)benzyl]aminomethyl}pyridin-2-ylamino)acetic acidYield 85.1%

Procedure

Reaction and post-treatment were carried out in the same manner as in Example 21-(b) except for using tert-butyl[tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(4-trifluoromethylthiazol-2-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate (440 mg, 0.611 mmol) obtained in Example 25-(a) in place of tert-butyl[tert-butoxycarbonyl(6-{[4-(pyrazol-1-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetate to afford the title compound (293 mg) as a white solid. (Yield: 85%)

Workup

  1. customReaction

Sources & evidence

ORD record
ord-56b90464d8e74843a13fe814a9f86a44
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

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