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

HRID 2359802Notes

Reaction equation

HRID 2359802 reaction equation
C([O:5][C:6](=[O:46])[CH2:7][N:8](C(OC(C)(C)C)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[CH:27][CH:26]=[N:25]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>>[F:38][C:35]1[CH:36]=[CH:37][C:32]([S:29]([CH:15]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[CH:27][CH:26]=[N:25]3)=[CH:20][CH:19]=2)[C:11]2[N:10]=[C:9]([NH:8][CH2:7][C:6]([OH:46])=[O:5])[CH:14]=[CH:13][CH:12]=2)(=[O:30])=[O:31])=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 86651782Tert-butyl [tert-butoxycarbonyl(6-{[4-(pyrazol-1-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-yl)amino}acetateHCID 86651787Tert-butyl [tert-butoxycarbonyl(6-{(4-fluorobenzenesulfonyl)[4-(pyrazol-1-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate

Product 1

HCID 66717464(6-{(4-Fluorobenzenesulfonyl)[4-(pyrazol-1-yl)benzyl]aminomethyl}pyridin-2-ylamino)acetic acidYield 86%

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-{(4-fluorobenzenesulfonyl)[4-(pyrazol-1-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate (794 mg, 1.22 mmol) obtained in Example 26-(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 (517 mg) as a white solid. (Yield: 86%)

Workup

  1. customReaction

Sources & evidence

ORD record
ord-1256a4fc4f2e43dab953011d0463d6b6
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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