Hydrochloric Acid → HCID 57820056, compound

HRID 1714172Notes

Reaction equation

HRID 1714172 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:48])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([C:24]([NH:39][CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][O:45][CH2:44][CH2:43]2)([C:26](=[O:38])[NH:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[CH3:25])=[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:48])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([C:24]([NH:39][CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][O:45][CH2:44][CH2:43]2)([C:26](=[O:38])[NH:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:35])([F:36])[F:37])=[CH:30][CH:29]=2)[CH3:25])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57820019HCID 57820019, compound2×

Product 1

HCID 57820056HCID 57820056, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-[2-(3-{4-[1-(2-Morpholin-4-yl-ethylamino)-1-(4-trifluoromethyl-phenylcarbamoyl)-ethyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (crude material from Example 24) was treated with 1.25M HCl in methanol (2.8 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 the desired product (35 mg, 13%). MS: calc'd 582 (MH+), exp 582 (MH+). 1H NMR (d6-DMSO, 400 MHz) δ 10.5 (broad s, 1H), 9.39 (s, 1H), 7.88 (d, 2H, J=8.8 Hz), 7.68 (d, 2H, J=8.8 Hz), 7.62 (d, 2H, J=8.4 Hz), 7.57 (d, 2H, J=8.4 Hz), 7.54 (d, 1H, J=15.6 Hz), 7.35 (d, 1H, J=7.6 Hz), 6.92 (t, 1H, J=7.6 Hz), 6.90 (d, 1H, J=15.6 Hz), 6.75 (dd, 1H, J=8.0 Hz, 1.2 Hz), 6.57 (td, 1H, J=8.0 Hz, 1.2 Hz), 4.93 (s, 2H), 3.53 (m, 4H), 3.33 (m, 2H, overlapped with DMSO solvent residual peak), 2.55 (m, 2H), 2.30 (m, 4H), 1.65 (s, 3H).

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-4edf2a7b953845259ad876fdac41d858
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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