Diisopropylethylamine → HCID 57226830, compound

HRID 1357866Notes

Reaction equation

HRID 1357866 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:20](O)=[O:21])[CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[NH2:56][C:57]1[CH:62]=[CH:61][C:60]([C@H:63]([CH3:70])[CH2:64][C:65]([O:67][CH2:68][CH3:69])=[O:66])=[CH:59][CH:58]=1>CN(C)C=O.C(OCC)(=O)C>[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:20]([NH:56][C:57]2[CH:58]=[CH:59][C:60]([C@H:63]([CH3:70])[CH2:64][C:65]([O:67][CH2:68][CH3:69])=[O:66])=[CH:61][CH:62]=2)=[O:21])[CH:3]=1

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 53963459HCID 53963459, compound

Product 1

HCID 57226830HCID 57226830, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 2-(4-methyl-2-o-tolylaminobenzoxazol-6-yl)acetic acid [0.1 g, Reference Example 9(b)] in dimethylformamide (3 mL) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.128 g), diisopropylethylamine (0.22 g) and after 5 minutes with ethyl (R) 3-(4-aminophenyl)butanoate (0.107 g, Reference Example 1). After 4 hours the reaction mixture was diluted with ethyl acetate and then washed with water, then with hydrochloric acid (1M), then twice with water, then with brine, then dried and then evaporated to give the title compound (0.15 g) as a brown oil.

Workup

  1. washwashed with water
  2. dry with materialwith hydrochloric acid (1M), then twice with water, then with brine, then dried
  3. customevaporated

Sources & evidence

ORD record
ord-d7ff232d3e9f4cb684f412885bcfbc24
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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