HCID 67531620, compound → HCID 67531311, compound

HRID 1506812Notes

Reaction equation

[ClH:1].[NH2:2][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([NH:12][C:13]([C:15]3C=[CH:22][CH:21]=[CH:20][C:16]=3[C:17](O)=O)=[O:14])[CH:10]=[CH:11][C:5]=2[N:4]=1.NC1C=CC2N=C(N(C(OC(C)(C)C)=O)[C:34]([O:36]C(C)(C)C)=[O:35])N(C(OC(C)(C)C)=O)C=2C=1>>[ClH:1].[NH2:2][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([NH:12][C:13](=[O:14])[CH2:15][C:16]3([CH2:17][C:34]([OH:36])=[O:35])[CH2:20][CH2:21][CH2:22]3)[CH:10]=[CH:11][C:5]=2[N:4]=1

Participants

Reactant 2

HCID 67531620HCID 67531620, compound

HCID 67531839HCID 67531839, compound

Product 1

HCID 67531311HCID 67531311, compoundYield 85%

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 (0.167 g, 0.372 mmol) was reacted with (S)-7-oxaspiro[3.5]nonane-6,8-dione (0.057 g, 0.372 mmol) to give the title product (0.107 g, 85% yield) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 7.49 (s, 1H), δ 6.95 (s, 2H), δ 2.24 (m, 4H), δ 1.32 (m, 8H) ppm; 13C NMR (75 MHz, CD3OD) δ 175.2, 173.8, 171.8, 151.9, 135.0, 129.7, 116.7, 111.3, 103.9, 44.4, 43.9, 42.0, 39.7, 37.8, 24.1 ppm; HRMS (ESI) Calcd for C15H18N4O3(M+) 302.1379. Found 302.1373.

Sources & evidence

ORD record: ord-61bf66196391440da7c3fc725e7b6bb5
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221765B2

Reaction notes

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