Hydrochloric Acid → HCID 59224702, compound

HRID 1811763Notes

Reaction equation

HRID 1811763 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:13][C:14]1[N:19]=[C:18]([C:20]2[C:21]([CH3:56])=[CH:22][C:23]([CH3:55])=[C:24]([CH:54]=2)[C:25]([NH:27][CH2:28][C:29]2([CH2:33][NH:34][C:35]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:32][O:31][CH2:30]2)=[O:26])[CH:17]=[C:16](Cl)[N:15]=1.Cl>CN(C)C=O>[NH2:13][C:14]1[N:15]=[C:16]([S:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH:17]=[C:18]([C:20]2[CH:54]=[C:24]([C:25](=[O:26])[NH:27][CH2:28][C:29]3([CH2:33][NH:34][C:35]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:32][O:31][CH2:30]3)[C:23]([CH3:55])=[CH:22][C:21]=2[CH3:56])[N:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 65143-Mercaptopropionic AcidHCID 10796Cesium carbonateHCID 59224699HCID 59224699, compound

Product 1

HCID 59224702HCID 59224702, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-Mercaptopropionic acid (84 μl, 0.937 mmol) and cesium carbonate (316 mg, 0.970 mmol) were added to an N,N-dimethylformamide (1.0 ml) solution of 5-(2-amino-6-chloropyrimidin-4-yl)-2,4-dimethyl-N-{3-[(tritylamino)methyl]oxetan-3-ylmethyl}benzamide (119 mg, 0.192 mmol) obtained in Step 2 above. The resulting mixture was stirred at 80° C. for 1.5 hour. The reaction solution was slightly acidified with 1N hydrochloric acid, and the precipitated solid was collected by filtration. The separated solid was washed with water, and then dried under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: dichloromethane:methanol=15:1) to yield 3-{2-amino-6-[2,4-dimethyl-5-({3-[(tritylamino)methyl]oxetan-3-ylmethyl}carbamoyl)phenyl]pyrimidin-4-ylsulfanyl}propanoic acid (77 mg) as a white solid material.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washThe separated solid was washed with water
  3. customdried under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (developing solvent: dichloromethane:methanol=15:1)

Sources & evidence

ORD record
ord-a9b4be8baa1845e8bbd54ad9c01c777e
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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