826-62-0 → HCID 67532003, compound

HRID 1506814Notes

Reaction equation

HRID 1506814 reaction equation
[ClH:1].[NH2:2][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([NH:12][C:13]([C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[C:17]([OH:19])=[O:18])=[O:14])[CH:10]=[CH:11][C:5]=2[N:4]=1.N[C:25]1C=CC2N=C(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)N(C(OC(C)(C)C)=O)C=2C=1.C12CC(C=C1)C1C(OC(=O)C21)=O>>[ClH:1].[NH2:2][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([NH:12][C:13]([C@@H:15]3[CH:23]4[CH2:25][CH:20]([CH:21]=[CH:22]4)[C@@H:16]3[C:17]([OH:19])=[O:18])=[O:14])[CH:10]=[CH:11][C:5]=2[N:4]=1

Participants

4

Reactant 3

HCID 13223826-62-0HCID 67531620HCID 67531620, compoundHCID 67531839HCID 67531839, compound

Product 1

HCID 67532003HCID 67532003, compoundYield 94%

Procedure

Following the same procedure to synthesize 2-(2-amino-1H-benzo[d]imidazol-6-ylcarbamoyl)benzoic acid hydrochloride (8), tert-butyl 6-amino-2-(bis(tert-butoxycarbonyl)amino)-1H-benzo[d]imidazole-1-carboxylate (0.114 g, 0.254 mmol) was reacted with Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (0.042 g, 0.254 mmol) to make the title product (0.084 g, 94% yield) as a white solid. 1H NMR (300 MHz, CD3OD) δ 7.35 (d, 1H), δ 7.13 (s, 1H), δ 6.99 (d, 1H), δ 6.23 (s, 2H), δ 3.51 (s, 2H), δ 3.37 (s, 2H), δ 1.68 (dd, 2H) ppm; 13C NMR (75 MHz, CD3OD) δ 178.1, 151.7, 134.8, 134.6, 130.6, 129.8, 129.6, 128.1, 122.8, 111.5, 110.7, 52.0, 46.8, 45.9, 45.5, 45.4 ppm; HRMS (ESI) Calcd for C16H16N4O3 (M+) 312.1222. Found 312.1226.

Sources & evidence

ORD record
ord-3ee5dcb767be408491d55f483b8663f2
Source dataset
uspto-grants-2015_12
Patent number
US09221765B2

Reaction notes

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