Hydrochloric Acid → HCID 50942502, compound

HRID 1714176Notes

Reaction equation

HRID 1714176 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:49])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([N:38](C=O)[CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[C:25](=[O:37])[NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F: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:49])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([NH:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[C:25](=[O:37])[NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57820116HCID 57820116, compound

Product 1

HCID 50942502HCID 50942502, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-[2-(3-{4-[[Formyl-(2-morpholin-4-yl-ethyl)-amino]-(4-trifluoromethyl-phenylcarbamoyl)-methyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (300 mg, 0.432 mmol) was treated with 1.25M HCl in methanol (2.6 mL) 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 the desired product (58 mg, 24%). MS: calc'd 568 (MH+) exp 568 (MH+). 1H NMR (d6-DMSO, 400 MHz) δ 10.6 (broad s, 1H), 9.40 (s, 1H), 7.84 (d, 2H, J=8.4 Hz), 7.69 (d, 2H, J=8.4 Hz), 7.62 (d, 2H, J=8.0 Hz), 7.54 (d, 2H, J=8.0 Hz), 7.53 (d, 1H, J=15.6 Hz), 7.33 (d, 1H, J=7.6 Hz), 6.91 (t, 1H, J=7.6 Hz), 6.89 (d, 1H, J=15.6 Hz), 6.75 (d, 1H, J=7.2 Hz), 6.58 (t, 1H, J=7.2 Hz), 4.94 (broad s, 2H), 4.51 (broad s, 1H), 3.59 (m, 4H), 3.45 (m, 2H), 2.66 (m, 2H), 2.33 (m, 4H).

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-88badcfc0b2e408698f77540d07f514e
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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