Hydrogen Bromide → HCID 67363707, compound

HRID 1242204Notes

Reaction equation

HRID 1242204 reaction equation
C[O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-])=O)=[C:5]([N+:14]([O-])=O)[CH:4]=1.CO[C:19](OC)(OC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.COC1C(OC)=CC2N[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=NC=2C=1.N1C2C=CC=CC=2NC=1.CC1C=CC(B(O)O)=CC=1.COC1C(OC)=CC2N(C3C=CC(C)=CC=3)C(C3C=CC=CC=3)=NC=2C=1.Br.OC1C(O)=CC2N(C3C=CC(C)=CC=3)C(C3C=CC=CC=3)=NC=2C=1.[CH:119]([O:122][C:123](=[O:130])[CH2:124][CH2:125][CH2:126][CH2:127]CBr)([CH3:121])[CH3:120].C(OC(=O)CCCCCOC1C(O)=CC2N=C(C3C=CC=CC=3)N(C3C=CC(C)=CC=3)C=2C=1)(C)C>CCOCC>[CH:119]([O:122][C:123](=[O:130])[CH2:124][CH2:125][CH2:126][CH2:127][CH2:10][O:9][C:8]1[C:3]([OH:2])=[CH:4][C:5]2[N:14]([C:23]3[CH:22]=[CH:21][C:20]([CH3:19])=[CH:25][CH:24]=3)[C:37]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[N:11][C:6]=2[CH:7]=1)([CH3:121])[CH3:120]

Participants

12

Reactant 10

HCID 260Hydrogen BromideHCID 5798BenzimidazoleHCID 69720Trimethyl orthobeznoateHCID 79799Tolylboronic acidHCID 2229891,2-Dimethoxy-4,5-dinitrobenzeneHCID 549816Isopropyl 6-bromohexanoateHCID 11995863HCID 11995863, compoundHCID 21937997HCID 21937997, compoundHCID 21938036HCID 21938036, compoundHCID 219381695,6-Dimethoxy-2-phenyl-1H-benzimidazole

Product 1

HCID 67363707HCID 67363707, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4,5-Dimethoxy-1,2-dinitrobenzene was hydrogenated to the diamino compound according to general operating instructions 1, and said compound was cyclized with trimethyl orthobenzoate to 5,6-dimethoxy-2-phenyl-1H-benzimidazole (flash point 131-133° C.) as crude product according to general operating instructions 3. This benzimidazole derivative was reacted with 4-methylphenylboronic acid to 5,6-dimethoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole (flash point 145-148° C.) according to general operating instructions 14. After ether cleavage with hydrobromic acid according to general operating instructions 6 to 5,6-dihydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole (1H-NMR of hydrobromide (D6-DMSO): δ=2.42 ppm s (3H); 6.68 s (1H); 7.22 s (1H); 7.40-7.62 m (10H)), it was alkylated with 6-bromohexanoic acid isopropyl ester according to general operating instructions 8. 6-[[5-Hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester

Sources & evidence

ORD record
ord-3538a39f1162485bb1397a0b8cb60515
Source dataset
uspto-grants-2006_10
Patent number
US07115645B2

Reaction notes

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