3,3-Dimethylglutaric anhydride → HCID 67532126, compound

HRID 1506811Notes

Reaction equation

[ClH:1].NC1NC2C=C(NC(C3C=CC=CC=3C(O)=O)=O)C=CC=2N=1.[NH2:24][C:25]1[CH:26]=[CH:27][C:28]2[N:32]=[C:31]([N:33](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[N:30](C(OC(C)(C)C)=O)[C:29]=2[CH:55]=1.[CH3:56][C:57]1([CH3:65])[CH2:62][C:61](=[O:63])[O:60][C:59](=[O:64])[CH2:58]1>>[ClH:1].[NH2:33][C:31]1[NH:30][C:29]2[CH:55]=[C:25]([NH:24][C:61](=[O:63])[CH2:62][C:57]([CH3:65])([CH3:56])[CH2:58][C:59]([OH:64])=[O:60])[CH:26]=[CH:27][C:28]=2[N:32]=1

Participants

Reactant 3

HCID 778133,3-Dimethylglutaric anhydride

HCID 67531620HCID 67531620, compound

HCID 67531839HCID 67531839, compound

Product 1

HCID 67532126HCID 67532126, compoundYield 93%

Procedure

Following the same procedure to synthesize 2-(2-amino-1H-benzo[d]imidazol-6-ylcarbamoyl)benzoic acid hydrochloride, tert-butyl 6-amino-2-(bis(tert-butoxycarbonyl)amino)-1H-benzo[d]imidazole-1-carboxylate (0.157 g, 0.351 mmol) was reacted with 4,4-dimethyldihydro-2H-pyran-2,6(3H)-dione (0.049 g, 0.351 mmol) to give the title product (0.107 g, 93% yield) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 7.81 (s, 1H), δ 7.29 (m, 2H), δ 2.45 (m, 4H), 1.16 (m, 6H) ppm; 13C NMR (75 MHz, CD3OD) 174.8, 173.6, 173.1, 171.9, 171.6, 151.2, 134.7, 129.6, 111.5, 103.9, 33.2, 33.1, 29.1, 27.3, 26.9 ppm; HRMS (ESI) Calcd for C14H19N4O3 (M+) 290.1378. Found 290.1380.

Sources & evidence

ORD record: ord-57114da5f9114877b2e759d172b849c5
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221765B2

Reaction notes

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