3,3-Dimethylglutaric anhydride → HCID 67532016, compound

HRID 1506810Notes

Reaction equation

[ClH:1].NC1NC2C=C(N3C(=O)C=CC3=O)C=CC=2N=1.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]2[N:27]=[C:26]([N:28](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[N:25](C(OC(C)(C)C)=O)[C:24]=2[CH:50]=1.[CH3:51][C:52]1([CH3:60])[CH2:57][C:56](=[O:58])[O:55][C:54](=O)[CH2:53]1>>[ClH:1].[NH2:28][C:26]1[NH:25][C:24]2[CH:50]=[C:20]([N:19]3[C:54](=[O:55])[CH2:53][C:52]([CH3:60])([CH3:51])[CH2:57][C:56]3=[O:58])[CH:21]=[CH:22][C:23]=2[N:27]=1

Participants

Reactant 3

HCID 778133,3-Dimethylglutaric anhydride

HCID 67531620HCID 67531620, compound

HCID 178479113HCID 178479113, compound

Product 1

HCID 67532016HCID 67532016, compoundYield 98%

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 (0.300 g, 0.669 mmol) was reacted with 4,4-dimethyldihydro-2H-pyran-2,6(3H)-dione (0.095 g, 0.669 mmol) to give the title product (0.202 g, 98% yield) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 7.86 (s, 1H), δ 7.28 (s, 2H), δ 2.49 (s, 2H), δ 2.39 (s, 2H), δ 1.15 (s, 6H) ppm; 13C NMR (75 MHz, CD3OD) 174.8, 171.7, 151.2, 134.9, 129.8, 126.1, 116.4, 111.3, 103.8, 45.4, 33.1, 27.2 ppm; HRMS (ESI) Calcd for C14H16N4O2 (M+) 272.1273. Found 272.1282.

Sources & evidence

ORD record: ord-66aaff0ca00744c5b06fdfc1917724a1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221765B2

Reaction notes

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