Pyridine → HCID 118271847, compound

HRID 590865Notes

Reaction equation

HRID 590865 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[NH2:7][C:8]1[C:12]2[CH:13]=[N:14][C:15]([NH:17][C:18]([NH:20][C@@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:22])=[O:19])=[CH:16][C:11]=2[N:10]([C:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:9]=1.N1C=CC=CC=1.C(O)C(N)(CO)CO>C(Cl)Cl>[CH3:1][O:2][CH2:3][C:4]([NH:7][C:8]1[C:12]2[CH:13]=[N:14][C:15]([NH:17][C:18]([NH:20][C@@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:22])=[O:19])=[CH:16][C:11]=2[N:10]([C:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[N:9]=1)=[O:5]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 96623Methoxyacetyl chlorideHCID 118271680HCID 118271680, compound

Product 1

HCID 118271847HCID 118271847, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an 8 mL vial charged with 2-methoxyacetyl chloride (6.6 mg, 0.061 mmol) was added (R)-1-(3-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (30 mg, 0.056 mmol) in DCM (1 ml) and pyridine (0.045 ml, 0.557 mmol). The vial was capped and the contents stirred at room temperature for 16 h. The reaction mixture was diluted with DCM (1 mL), MP-Trisamine (137 mg, 0.278 mmol) added, and the contents of the vial shaken at room temperature for 3 h. The resin was filtered, and washed through with DCM (1 mL). The volatiles were removed in vacuo to afford crude (R)-2-methoxy-N-(6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide, which was taken forward without purification. MS ESI calc'd. For C37H35N6O3 [M+H]+ 611. found 611.

Workup

  1. customThe vial was capped
  2. additionadded
  3. stirringthe contents of the vial shaken at room temperature for 3 h
  4. filtrationThe resin was filtered
  5. washwashed through with DCM (1 mL)
  6. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-c698db372afa4c4294bcc552d195212b
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

Loading…