Diisopropylethylamine → (3RS)-3-{5-[2-(4-methyl-2-o-tolylamino-benzoxazol-6-yl)acetylamino]pyrid-2-yl}butyric acid ethyl ester

HRID 49698Notes

Reaction equation

HRID 49698 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[O:10][C:6]=2[CH:5]=[C:4]([CH2:19]C(O)=O)[CH:3]=1.F[P-](F)(F)(F)(F)F.N1([O:39][C:40](N(C)C)=[N+:41](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.N[C:57]1[CH:62]=[CH:61][N:60]=[C:59]([CH:63]([CH3:70])[CH2:64][C:65]([O:67][CH2:68][CH3:69])=[O:66])[CH:58]=1>CN(C)C=O.O>[CH2:68]([O:67][C:65](=[O:66])[CH2:64][CH:63]([C:59]1[CH:58]=[CH:57][C:62]([NH:41][C:40](=[O:39])[CH2:19][C:4]2[CH:3]=[C:2]([CH3:1])[C:7]3[N:8]=[C:9]([NH:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[CH3:18])[O:10][C:6]=3[CH:5]=2)=[CH:61][N:60]=1)[CH3:70])[CH3:69]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18188094HCID 18188094, compoundHCID 86586440ethyl (3RS)-3-(4-aminopyrid-2-yl)butyrate

Product 1

HCID 69687901(3RS)-3-{5-[2-(4-methyl-2-o-tolylamino-benzoxazol-6-yl)acetylamino]pyrid-2-yl}butyric acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 2-(4-methyl-2-o-tolylamino-benzoxazol-6-yl)acetic acid (0.13 g, Reference Example 9) in dimethylformamide (5 mL) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.166 g), diisopropylethylamine (0.153 mL) and then with a solution of ethyl (3RS)-3-(4-aminopyrid-2-yl)butyrate (0.091 g, Reference Example 5) in dimethylformamide (5 mL). After stirring for 1 hour and then standing at room temperature over night the reaction mixture was diluted with water and then extracted with t-butyl methyl ether. The extracts were dried over magnesium sulphate and then evaporated to give (3RS)-3-{5-[2-(4-methyl-2-o-tolylamino-benzoxazol-6-yl)acetylamino]pyrid-2-yl}butyric acid ethyl ester as a gum. A solution of this gum in ethanol was treated with aqueous lithium hydroxide solution (1M) and after stirring at room temperature for 1 hour the mixture was partially evaporated. The residue was acidified to pH 6-7 by addition of concentrated hydrochloric acid. This mixture was extracted with ethyl acetate. The extracts were dried over magnesium sulphate and then evaporated to give the title compound (0.012 g) as a cream solid. MS (ES negative): 457(MH−).

Workup

  1. waitstanding at room temperature over night
  2. extractionextracted with t-butyl methyl ether
  3. dry with materialThe extracts were dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-03dab6990a2d4f22a79377dfa272f00a
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

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