Hydrochloric Acid → HCID 18929584, compound

HRID 1599070Notes

Reaction equation

HRID 1599070 reaction equation
C([O:5][C:6](=[O:51])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([NH:16][CH:17]2[C:23](=[O:24])[N:22]([C:25]([CH:37]([CH3:39])[CH3:38])([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:26](=[O:28])[NH2:27])[C:21]3[CH:40]=[CH:41][CH:42]=[CH:43][C:20]=3[N:19]([C:44]3[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=3)[C:18]2=[O:50])=[O:15])[CH:8]=1)(C)(C)C.Cl.CCOCC>O1CCOCC1>[CH:37]([C:25]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)([C:26](=[O:28])[NH2:27])[N:22]1[C:23](=[O:24])[CH:17]([NH:16][C:14](=[O:15])[NH:13][C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[C:6]([OH:51])=[O:5])[C:18](=[O:50])[N:19]([C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)[C:20]2[CH:43]=[CH:42][CH:41]=[CH:40][C:21]1=2)([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 86752410HCID 86752410, compound

Product 1

HCID 18929584HCID 18929584, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 3-(3-{1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}-ureido)-benzoic acid tert butyl ester (115 mg, 0.224 mmol) and 4N HCl in dioxane (1 ml) was stirred at rt for 1.75 h after which time a further 1 ml of 4N HCl in dioxane was added and the reaction mixture stirred at rt overnight. Ether (20 ml) was added and the resultant precipitate was triturated with ether (3×30 ml) to afford the title compound as a white powder. 1H NMR (300 MHz, CDCl3).s 1H NMR (300 MHz, CDCl-3). s 8.61 (s, 1H), 8.56 (d, 1H, J=8.2), 7.91 (d, 1H, J=8.2), 6.91-7.83 (m, 16H), 6.41 (d, 1H, J=7.9), 5.43 (d, 1H, J=7.9), 4.91 (sept, 1H, J=6.8), 4.60 (d, 1H, J=11.8), 4.18 (d, 1H, J=11.8), 3.86 (s, 3H), 1.06 (m, 6H). Low resolution MS (FAB) m/e 637 (m+).

Workup

  1. additionwas added
  2. customthe resultant precipitate was triturated with ether (3×30 ml)

Sources & evidence

ORD record
ord-b466635aa81a4ce79293ee5a03472468
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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