Hydrochloric Acid → HCID 70089684, compound

HRID 2186054Notes

Reaction equation

Cl.[NH2:2][N:3]=[CH:4][C:5]1[CH:37]=[CH:36][C:8]([C:9]([NH:11][C:12]2[CH:35]=[CH:34][C:15]3[CH2:16][N:17]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:18](=[O:25])[CH:19]([CH2:21]C(O)=O)[NH:20][C:14]=3[CH:13]=2)=[O:10])=[CH:7][CH:6]=1>>[NH2:2][N:3]=[CH:4][C:5]1[CH:37]=[CH:36][C:8]([C:9]([NH:11][C:12]2[CH:35]=[CH:34][C:15]3[CH2:16][N:17]([CH2:26][CH2:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:18](=[O:25])[C:19]([CH3:21])=[N:20][C:14]=3[CH:13]=2)=[O:10])=[CH:7][CH:6]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 70078477HCID 70078477, compound

Product 1

HCID 70089684HCID 70089684, compound

Procedure

Using the procedure of Preparation 26(e), except substituting TFA for hydrochloric acid, yielded a mixture of 8-[[4-(aminoiminomethyl)benzoyl]-amino]-2,3,4,5-tetrahydro-3-oxo-4-(2-phenylethyl)-1H-1,4-benzodiazepine-2-acetic acid and the title compound (80 mg) which were separated by HPLC RT 24.8 min (YMC ODS AQ, 50×250 mm, 85 mL/min, 30% AN/W-TFA, UV detection at 220 nm); 1H NMR (400 MHz, MeOD4) δ8.1(d, 2H), 7.9(d, 2H), 7.75(s, 1H),7.60(d, 1H), 7.35(d, 1H), 7.22-7.12(m, 5H), 4.20(m, 2H), 3.70(m, 2H), 2.85(m, 2H), 2.42(s, 3H); MS(ES) m/e 440 [M+H]+.

Workup

customyielded
customthe title compound (80 mg) which were separated by HPLC RT 24.8 min (YMC ODS AQ, 50×250 mm, 85 mL/min, 30% AN/W-TFA, UV detection at 220 nm)

Sources & evidence

ORD record: ord-09c6e7112d4746509a079f661270a720
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403578B1

Reaction notes

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