5-Hydroxyindoleacetic Acid → 2-(5-hydroxy-1H-indol-3-yl)-N-(1-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)-2-phenylethyl)acetamide

HRID 1506633

Reaction equation

HRID 1506633 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[C:29]2[CH2:35][C:36]([OH:38])=O.CCN(C(C)C)C(C)C.[CH3:48][C:49]1[N:50]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=2C)[C:51]([CH:54]([NH2:62])[CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[N:52][N:53]=1>CN(C=O)C>[OH:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[C:29]2[CH2:35][C:36]([NH:62][CH:54]([C:51]1[N:50]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:49]([CH3:48])=[N:53][N:52]=1)[CH2:55][C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)=[O:38]

Participants

6

Reactant 4

HCID 18265-Hydroxyindoleacetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 902815191-(5-methyl-4-(o-tolyl)-4H-1,2,4-triazol-3-yl)-2-phenylethanamine

Product 1

HCID 902813382-(5-hydroxy-1H-indol-3-yl)-N-(1-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)-2-phenylethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

HATU (40 mg, 0.105 mmol) was added to a solution of 2-(5-hydroxy-1H-indol-3-yl)acetic acid (19.2 mg, 0.1 mmol) and DIPEA (0.02 mL, 0.12 mmol) in DMF (0.3 mL). After 10 minutes, 10F (29.2 mg, 0.1 mmol) in 0.2 mL of DMF was added to the reaction. The reaction was stirred for 2 hours. LC/MS shows desired product with a small amount of acid. Purified reaction mixture on prep reverse phase HPLC using 20-80% B over 20 min. (A=0.1% TFA/H2O; B=0.1% TFA/Acetonitrile). Combined pure fractions as determined by LC/MS and lyophilized to provide) to provide the desired product. 1H NMR (400 MHz, DMSO) δ 10.44 (s, 1H), 8.64-8.42 (m, 1H), 7.50-7.19 (m, 3H), 7.17-6.93 (m, 6H), 6.81 (dd, J=53.1, 21.8 Hz, 4H), 6.54 (d, J=8.8 Hz, 1H), 3.39-3.22 (m, 3H), 3.09-2.85 (m, 2H), 2.01 (d, J=15.7 Hz, 3H). MS (m/z) 452 [M+H]+.

Sources & evidence

ORD record
ord-c5a2da4a0eb2474d85c02c9a532c00e2
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Linked notes

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