[4-(4-[1,2,3]Triazol-1-yl-butyl)-phenyl]-[2-(5-trifluoromethoxy-1H-indol-2-yl)-oxazol-4-ylmethyl]-carbamic acid tert-butyl ester → [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-[2-(5-trifluoromethoxy-1H-indol-2-yl)-oxazol-4-ylmethyl]-amine

HRID 1392239Notes

Reaction equation

HRID 1392239 reaction equation
C(OC(=O)[N:7]([C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][N:38]2[CH:42]=[CH:41][N:40]=[N:39]2)=[CH:30][CH:29]=1)[CH2:8][C:9]1[N:10]=[C:11]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=3)[O:12][CH:13]=1)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[N:38]1([CH2:37][CH2:36][CH2:35][CH2:34][C:31]2[CH:32]=[CH:33][C:28]([NH:7][CH2:8][C:9]3[N:10]=[C:11]([C:14]4[NH:15][C:16]5[C:21]([CH:22]=4)=[CH:20][C:19]([O:23][C:24]([F:26])([F:27])[F:25])=[CH:18][CH:17]=5)[O:12][CH:13]=3)=[CH:29][CH:30]=2)[CH:42]=[CH:41][N:40]=[N:39]1

Participants

4

Reactant 1

HCID 136331972[4-(4-[1,2,3]Triazol-1-yl-butyl)-phenyl]-[2-(5-trifluoromethoxy-1H-indol-2-yl)-oxazol-4-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 135510025[4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-[2-(5-trifluoromethoxy-1H-indol-2-yl)-oxazol-4-ylmethyl]-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[4-(4-[1,2,3]Triazol-1-yl-butyl)-phenyl]-[2-(5-trifluoromethoxy-1H-indol-2-yl)-oxazol-4-ylmethyl]-carbamic acid tert-butyl ester (0.31 g, 0.52 mmol) was stirred in a mixture of dichloro methane and trifluoro acetic acid (1:1, 10 ml) for 3 h. After concentration the crude product was purified on silica gel (ethyl acetate) yielding [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-[2-(5-trifluoromethoxy-1H-indol-2-yl)-oxazol-4-ylmethyl]-amine as light yellow solid.

Workup

  1. concentrationAfter concentration the crude product
  2. customwas purified on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-de17f4a3f68747ca874253488184bc96
Source dataset
uspto-grants-2008_03
Patent number
US07342030B2

Reaction notes

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