Formic Acid → HCID 178493063, compound

HRID 469812Notes

Reaction equation

HRID 469812 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[O:15][C:16]3[C:22]([C:23]4[CH:24]=[C:25]([NH2:30])[C:26]([NH2:29])=[CH:27][CH:28]=4)=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:31]CN=C=NCCCN(C)C.Cl.C(O)=O>CN(C1C=CN=CC=1)C.ClCCl>[NH:29]1[C:26]2[CH:27]=[CH:28][C:23]([C:22]3[C:16]4[O:15][C:14]([NH:13][C:5]5[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=5)=[N:18][C:17]=4[CH:19]=[CH:20][CH:21]=3)=[CH:24][C:25]=2[N:30]=[CH:31]1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67458022HCID 67458022, compound

Product 1

HCID 178493063HCID 178493063, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.16 g (0.228 mmol) 4-[2-(3,4,5-trimethoxy-phenylamino)-benzooxazol-7-yl]-benzene-1,2-diamine, 0.068 g (0.346 mmol) EDC-HCl, 0.043 g (0.345 mmol) DMAP, 0.012 g (0.27 mmol) formic acid), and 7 ml dichloromethane is stirred at room temperature for 20 h. Then the reaction mixture is concentrated in vacuo. The residue is purified by chromatography (silicagel, EtOAc:MeOH=9:1) to afford ca. the title compound. 4-[2-(3,4,5-trimethoxy-phenylamino)-benzooxazol-7-yl]-benzene-1,2-diamine is prepared from 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzene-1,2-diamine as described in Example 1.

Workup

  1. concentrationThen the reaction mixture is concentrated in vacuo
  2. customThe residue is purified by chromatography (silicagel, EtOAc:MeOH=9:1)

Sources & evidence

ORD record
ord-b630087b5c6f4118bef90e70e684866f
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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