Hydrochloric Acid → HCID 44158755, compound

HRID 1714160Notes

Reaction equation

HRID 1714160 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:44])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:31](=[O:43])[NH:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:35][CH:34]=2)[NH:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[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:44])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:31](=[O:43])[NH:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]([CH3:40])([CH3:41])[CH3:42])=[CH:37][CH:38]=2)[NH:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57820050HCID 57820050, compound2×

Product 1

HCID 44158755HCID 44158755, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-[2-(3-{4-[(4-tert-Butyl-phenylcarbamoyl)-(2-dimethylamino-ethylamino)-methyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (crude material from Example 8) was treated with 1.25M HCl in methanol (2 mL) at room temperature for 2 hours. 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 16 mg desired product (24% over two steps). MS: calc'd 514 (MH+) exp 514 (MH+). 1H NMR (CD3OD, 400 MHz) δ 7.79 (d, 1H, J=15.6 Hz), 7.74 (d, 2H, J=8.2 Hz), 7.68 (d, 2H, J=8.2 Hz), 7.49 (d, 2H, J=8.4 Hz), 7.37 (d, 2H, J=8.2 Hz), 7.36 (m, 4H), 6.93 (d, 1H, J=15.6 Hz), 3.40 (t, 2H, J=6.2 Hz), 3.23 (t, 2H, J=6.2 Hz), 2.95 (s, 6H), 1.31 (s, 9H).

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-f779607bab664760b3f0b415caab3e56
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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