2-Methoxyphenylacetic acid → 2-(2-methoxyphenyl)-N-(5-((1S,3S)-3-(5-(2-(pyridin-2-yl)acetamido)-1,3,4-thiadiazol-2-yl)cyclohexyl)-1,3,4-thiadiazol-2-yl)acetamide

HRID 572945Notes

Reaction equation

HRID 572945 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C@H:7]2[CH2:12][CH2:11][CH2:10][C@H:9]([C:13]3[S:17][C:16]([NH:18][C:19](=[O:27])[CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:15][N:14]=3)[CH2:8]2)=[N:4][N:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][C:37](O)=[O:38].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C)C=O.O>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][C:37]([NH:1][C:2]1[S:6][C:5]([C@H:7]2[CH2:12][CH2:11][CH2:10][C@H:9]([C:13]3[S:17][C:16]([NH:18][C:19](=[O:27])[CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:15][N:14]=3)[CH2:8]2)=[N:4][N:3]=1)=[O:38]

Participants

7

Reactant 4

HCID 71342-Methoxyphenylacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 76281118N-(5-((1S,3S)-3-(5-amino-1,3,4-thiadiazol-2-yl)cyclohexyl)-1,3,4-thiadiazol-2-yl)-2-(pyridin-2-yl)acetamide

Product 1

HCID 867191202-(2-methoxyphenyl)-N-(5-((1S,3S)-3-(5-(2-(pyridin-2-yl)acetamido)-1,3,4-thiadiazol-2-yl)cyclohexyl)-1,3,4-thiadiazol-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(5-((1S,3S)-3-(5-amino-1,3,4-thiadiazol-2-yl)cyclohexyl)-1,3,4-thiadiazol-2-yl)-2-(pyridin-2-yl)acetamide (50 mg, 0.12 mmol), 2-(2-methoxyphenyl)acetic acid (31.0 mg, 0.19 mmol), HATU (71.0 mg, 0.19 mmol), and N-ethyl-N-isopropylpropan-2-amine (29.0 mg, 0.22 mmol) in N,N-dimethylformamide (5 ml) was stirred at 50 degree overnight. The mixture was poured into water (10 ml), the precipitate was filtered to give the crude product. The crude product was purified by a standard method to give the desired product.

Workup

  1. filtrationthe precipitate was filtered
  2. customto give the crude product
  3. customThe crude product was purified by a standard method

Sources & evidence

ORD record
ord-7dec16b3ec9b4524b1e717d358bd0bd7
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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