Glutaric anhydride → HCID 67532267, compound

HRID 1506807Notes

Reaction equation

HRID 1506807 reaction equation
[ClH:1].[NH2:2][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([N:12]3[C:16](=[O:17])[CH:15]=[CH:14][C:13]3=[O:18])[CH:10]=[CH:11][C:5]=2[N:4]=1.N[C:20]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.C1(=O)OC(=O)CCC1>>[ClH:1].[NH2:2][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([N:12]3[C:13](=[O:18])[CH2:20][CH2:14][CH2:15][C:16]3=[O:17])[CH:10]=[CH:11][C:5]=2[N:4]=1

Participants

4

Reactant 3

HCID 7940Glutaric anhydrideHCID 67531620HCID 67531620, compoundHCID 178479113HCID 178479113, compound

Product 1

HCID 67532267HCID 67532267, compoundYield 93%

Procedure

Following the same procedure to synthesize 1-(2-amino-1H-benzo[d]imidazol-6-yl)-1H-pyrrole-2,5-dione hydrochloride, tert-butyl 6-amino-2-(bis(tert-butoxycarbonyl)amino)-1H-benzo[d]imidazole-1-carboxylate (0.113 g, 0.252 mmol) was reacted with glutaric anhydride (0.029 g, 0.252 mmol) to give the title compound (0.066 g, 93% yield) as a white solid. 1H NMR (300 MHz, CD3OD) δ 7.85 (s, 1H), δ 7.28 (s, 2H), δ 2.42 (m, 4H), δ 1.97 (m, 2H) ppm; 13C NMR (75 MHz, CD3OD) δ 174.1, 172.6, 135.2, 129.8, 125.9, 103.6, 35.6, 32.9, 20.9 ppm; HRMS (ESI) Calcd for C12H12N4O2 (M+) 244.0960. Found 244.0969.

Sources & evidence

ORD record
ord-887639567cb14a449c56343b539c93ea
Source dataset
uspto-grants-2015_12
Patent number
US09221765B2

Reaction notes

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