Acetic Acid → (R)-3-((1-((R)-6-((2,2-dimethylethylamino)methyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-1H-1,2,3-triazol-4-yl)methyl)-4-(4-methylbenzenesulfonyl)-3,4-dihydropyrazin-2(1H)-one

HRID 1432019Notes

Reaction equation

HRID 1432019 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[CH:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[C@@H:3]1[CH2:18][C:19]1[N:20]=[N:21][N:22]([C@@H:24]2[CH2:33][CH2:32][CH2:31][C:30]3[CH:29]=[C:28]([CH:34]=O)[CH:27]=[CH:26][C:25]2=3)[CH:23]=1.[C:36]([NH2:40])(C)(C)C.[CH3:41][C:42](O)=O.[BH-](OC(C)=O)(OC(C)=O)O[C:47](C)=O.[Na+]>ClCCCl>[CH3:47][CH:42]([CH3:41])[CH2:36][NH:40][CH2:34][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[C@H:24]([N:22]1[CH:23]=[C:19]([CH2:18][C@H:3]3[N:4]([S:8]([C:11]4[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=4)(=[O:9])=[O:10])[CH:5]=[CH:6][NH:7][C:2]3=[O:1])[N:20]=[N:21]1)[CH2:33][CH2:32][CH2:31]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6385Tert-ButylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57932484(R)-5-(4-(((R)-3-Oxo-1-(4-methylbenzenesulfonyl)-1,2,3,4-tetrahydropyrazin-2-yl)-methyl)-1H-1,2,3-triazol-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

Product 1

HCID 11570253(R)-3-((1-((R)-6-((2,2-dimethylethylamino)methyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-1H-1,2,3-triazol-4-yl)methyl)-4-(4-methylbenzenesulfonyl)-3,4-dihydropyrazin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(R)-5-(4-(((R)-3—Oxo-1-(4-methylbenzenesulfonyl)-1,2,3,4-tetrahydropyrazin-2-yl)-methyl)-1H-1,2,3-triazol-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde (1.1 mmol, 1 eq) was dissolved in DCE and treated with 4 Å powdered molecular sieves. To the solution was added t-butyl amine (3.2 mmol, 3.0 eq) and AcOH (3.2 mmol, 3.0 eq). The reaction stirred at RT overnight. NaBH(OAc)3 (3.3 mmol, 3.0 eq) was added and after 3 h, the solvent was removed and the residue was purified by SiO2 to afford amine the title compound (MS (m/z): 549.3 (m+H)).

Workup

  1. additiontreated with 4 Å
  2. customthe solvent was removed
  3. customthe residue was purified by SiO2

Sources & evidence

ORD record
ord-01ef3e5eb36846e6a86e9dd102b51b25
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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