Diisopropylethylamine → HCID 69142182, compound

HRID 1348948Notes

Reaction equation

HRID 1348948 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([CH2:17][C:18](O)=[O:19])[CH:14]=[CH:13][C:11]=2[N:12]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH2:55]([O:57][C:58](=[O:77])[CH2:59][CH:60]([C:67]1[CH:76]=[C:75]2[C:70]([CH2:71][CH2:72][NH:73][CH2:74]2)=[CH:69][CH:68]=1)[C:61]1[CH:66]=[CH:65][N:64]=[CH:63][CH:62]=1)[CH3:56]>CN(C)C=O>[CH2:55]([O:57][C:58](=[O:77])[CH2:59][CH:60]([C:61]1[CH:62]=[CH:63][N:64]=[CH:65][CH:66]=1)[C:67]1[CH:76]=[C:75]2[C:70]([CH2:71][CH2:72][NH:73][CH:74]2[C:18](=[O:19])[CH2:17][C:15]2[CH:14]=[CH:13][C:11]3[N:12]=[C:8]([NH:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=4[CH3:21])[O:9][C:10]=3[CH:16]=2)=[CH:69][CH:68]=1)[CH3:56]

Participants

6

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 235083152-(2-(O-tolylamino)benzo[d]oxazol-6-yl)acetic acidHCID 69141826HCID 69141826, compound

Product 1

HCID 69142182HCID 69142182, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2-o-tolylaminobenzoxazole-6-acetic acid (0.124 g) and diisopropylethylamine (0.17 g) in dimethylformamide (2 mL) was treated with a solution of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.183 g) in dimethylformamide. After 10 minutes at room temperature this yellow solution was added dropwise to a rapidly stirred solution of 3-(1,2,3,4-tetrahydro-isoquinolin-7-yl)-3-(pyrid-4-yl)-propionic acid ethyl ester, enantiomer A {0.219 mmoles, Reference Example 17(a)} in dimethylformamide. After stirring at room temperature for 2.5 hours the reaction mixture was evaporated. The residual oil was dissolved in a mixture of acetonitrile, water and trifluoroacetic acid (25:75:0.1) and treated with dimethylformamide and trifluoroacetic acid to bring to pH2. This mixture was subjected to preparative HPLC {Hypersil Elite C18 column, 10 cm×2.1 cm, using a mixture of acetonitrile, water and trifluoroacetic acid (25:75:0.1) as the mobile phase followed by a 1% acetonitrile/minute gradient) to give the title compound. LC-MS:MS (ES)=575 (M+H)+, 573 (M−H)−.

Workup

  1. customwas evaporated
  2. dissolutionThe residual oil was dissolved in a mixture of acetonitrile, water and trifluoroacetic acid (25:75:0.1)
  3. additiontreated with dimethylformamide and trifluoroacetic acid
  4. additiona mixture of acetonitrile, water and trifluoroacetic acid (25:75:0.1) as the mobile phase

Sources & evidence

ORD record
ord-087826bd808e4494aa44b7f532bbc478
Source dataset
uspto-grants-2007_05
Patent number
US07211586B2

Reaction notes

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