HCID 57820095, compound → HCID 44158754, compound

HRID 1714158Notes

Reaction equation

HRID 1714158 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:54])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([N:37](C(OC(C)(C)C)=O)[CH2:38][CH:39]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[CH3:40])[C:25](=[O:36])[NH:26][C:27]2[CH:32]=[CH:31][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:29][CH:28]=2)=[CH:20][CH:19]=1)(C)(C)C>Cl.CO>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:54])/[CH:16]=[CH:17]/[C:18]1[CH:19]=[CH:20][C:21]([CH:24]([C:25](=[O:36])[NH:26][C:27]2[CH:32]=[CH:31][C:30]([CH:33]([CH3:34])[CH3:35])=[CH:29][CH:28]=2)[NH:37][CH2:38][CH:39]([N:41]2[CH2:42][CH2:43][O:44][CH2:45][CH2:46]2)[CH3:40])=[CH:22][CH:23]=1

Participants

3

Reactant 1

HCID 57820095HCID 57820095, compound2×

Product 1

HCID 44158754HCID 44158754, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

(E)-[2-(3-{4-[[tert-Butoxycarbonyl-(2-morpholin-4-yl-propyl)-amino]-(4-isopropyl-phenylcarbamoyl)-methyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (crude product from Example 3) was dissolved in 1.25M HCl/MeOH (2.9 mL) and stirred at room temperature overnight. The reaction was quenched slowly with solid sodium bicarbonate until the pH was 6-7. The mixture was diluted in acetonitrile with a small amount of dimethylsulfoxide, passed through a 40 μm pipette filter, and then purified by preparative HPLC to obtain 150 mg desired product (56% over two steps). MS: calc'd 556 (MH+), exp 556 (MH+).

Workup

  1. customThe reaction was quenched slowly with solid sodium bicarbonate until the pH was 6-7
  2. additionThe mixture was diluted in acetonitrile with a small amount of dimethylsulfoxide
  3. filtrationfilter
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-321269f664154688b5a03c18ee8f578b
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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