Benzoic Acid → HCID 58382530, compound

HRID 1027499Notes

Reaction equation

HRID 1027499 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.N1(OC(=[N+](C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:32][CH2:33][CH:34]([OH:66])[CH2:35][O:36][C:37]1[C:42]([CH3:43])=[CH:41][C:40]([C:44]2[O:45][C:46]3[N:47]=[C:48]([CH2:57][C:58]4[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=4)[N:49]=[C:50]([O:53][CH2:54][CH2:55][CH3:56])[C:51]=3[N:52]=2)=[CH:39][C:38]=1[CH3:65].C(N(C(C)C)C(C)C)C>CN(C)C=O>[Cl:64][C:61]1[CH:60]=[CH:59][C:58]([CH2:57][C:48]2[N:49]=[C:50]([O:53][CH2:54][CH2:55][CH3:56])[C:51]3[N:52]=[C:44]([C:40]4[CH:39]=[C:38]([CH3:65])[C:37]([O:36][CH2:35][CH:34]([OH:66])[CH2:33][NH:32][C:1](=[O:9])[C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[C:42]([CH3:43])[CH:41]=4)[O:45][C:46]=3[N:47]=2)=[CH:63][CH:62]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58382527HCID 58382527, compound

Product 1

HCID 58382530HCID 58382530, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 37 mg of benzoic acid, 110 mg of [(benzotriazol-1-yloxy)-dimethylamino-methylene]-dimethyl-ammonium tetrafluoroborate (TBTU), 100 mg of 1-amino-3-{4-[5-(4-chloro-benzyl)-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (example 20) and 104 mg of ethyldiisopropylamine in 2 ml of dimethylformamide was stirred for 16 h at room temperature. After removal of the solvent the product was isolated via preparative HPLC (method HPLC2) to yield 11 mg of the title compound.

Workup

  1. customAfter removal of the solvent the product
  2. customwas isolated via preparative HPLC (method HPLC2)

Sources & evidence

ORD record
ord-e8718d453be74c14accf9d6b27e4e2f9
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

Loading…