HCID 67471938, compound → HCID 67283814, compound

HRID 1910676Notes

Reaction equation

HRID 1910676 reaction equation
[Cl:1][C:2]1[CH:47]=[CH:46][C:5]2[N:6]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)[C:7](=[O:36])[CH:8]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[N:9]=[C:10]([C:11]3[CH:12]=[C:13]4[N:19](C(OC(C)(C)C)=O)[C:18](=[O:27])[NH:17][C:14]4=[N:15][CH:16]=3)[C:4]=2[CH:3]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:47]=[CH:46][C:5]2[N:6]([CH2:37][C:38]3[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=3)[C:7](=[O:36])[CH:8]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[N:9]=[C:10]([C:11]3[CH:12]=[C:13]4[NH:19][C:18](=[O:27])[NH:17][C:14]4=[N:15][CH:16]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 67471938HCID 67471938, compound

Product 1

HCID 67283814HCID 67283814, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 6-(7-chloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-1-carboxylate (308 mg) was dissolved in 4 N HCl in dioxane (20 mL) and it was held at room temperature for an hour, then partitioned between aqueous sodium bicarbonate and EtOAc. The organic fraction was washed with brine, then dried over sodium sulfate, then concentrated and used further without purification (250 mg, 95% yield). 1H-NMR (300 MHz, CDCl3) δ 8.60 (bs, 1H), 8.10 (s, 1H), 7.80-7.10 (m, 14H), 6.90 (d, 2H), 6.62 (d, 2H), 5.65 (d, 1H), 4.55 (d, 1H), 3.95 (m, 1H), 3.80-3.60 (m, 8H), 1.60 (bs, 2H).

Workup

  1. waitit was held at room temperature for an hour
  2. custompartitioned between aqueous sodium bicarbonate and EtOAc
  3. washThe organic fraction was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customused further without purification (250 mg, 95% yield)

Sources & evidence

ORD record
ord-6d4a323b7e7b4c15950e4a5507c176c0
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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