3-Phenyllactic acid, (S)- → HCID 118108316, compound

HRID 930968Notes

Reaction equation

HRID 930968 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6]2[C:9]3[C:14]([NH:15][C:16]4[CH:25]=[CH:24][C:19]5[NH:20][C:21](=[O:23])[S:22][C:18]=5[CH:17]=4)=[N:13][CH:12]=[N:11][C:10]=3[S:26][C:5]=2[CH2:4]1.[OH:27][C@@H:28]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:29](O)=[O:30].F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[OH:27][C@H:28]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:29]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6]2[C:9]3[C:14]([NH:15][C:16]4[CH:25]=[CH:24][C:19]5[NH:20][C:21](=[O:23])[S:22][C:18]=5[CH:17]=4)=[N:13][CH:12]=[N:11][C:10]=3[S:26][C:5]=2[CH2:4]1)=[O:30]

Participants

6

Reactant 3

HCID 4447183-Phenyllactic acid, (S)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90014477HCID 90014477, compound

Product 1

HCID 118108316HCID 118108316, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture comprising 50 mg (130 μmol) (RS)-6-{[7-(aminomethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl]amino}-1,3-benzothiazol-2(3H)-one (prepared according to example 20), 4 mL N,N-dimethylforamide, 17.5 mg N,N-dimethylpyridin-4-amine, 21.7 mg (2S)-2-hydroxy-3-phenylpropanoic acid and 54.5 mg N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methylmethanaminium hexafluorophosphate was stirred at 23° C. overnight. The solvent was removed and the residue purified by chromatography to give 32 mg (45%) of the title compound.

Workup

  1. customThe solvent was removed
  2. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-cec31d3a572d4b5d8920d1e771a498f4
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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