Pyridine → HCID 118649739, compound

HRID 590859Notes

Reaction equation

HRID 590859 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[N:4]([C:23]([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)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.N1C=CC=CC=1.Cl[C:49]([O:51][CH2:52][CH3:53])=[O:50].C(O)C(N)(CO)CO>C(Cl)Cl>[CH2:52]([O:51][C:49](=[O:50])[NH:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[N:4]([C:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([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)[N:3]=1)[CH3:53]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 10928Ethyl chloroformateHCID 118271680HCID 118271680, compound

Product 1

HCID 118649739HCID 118649739, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an 8 mL vial charged with (R)-1-(3-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (20 mg, 0.037 mmol) in DCM (1 ml) was added pyridine (0.1 ml) followed by ethyl chloroformate (10.70 μl, 0.111 mmol). The vial was capped and the contents stirred at room temperature for 16 h. Un-reacted chloroformate was quenched by adding MP-Trisamine (91 mg, 0.186 mmol) and tumbling the vial for an additional 3 h. The resin was filtered and the volatiles removed in vacuo to afford crude (R)-ethyl(6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate which was taken forward without purification. MS ESI calc'd. For C37H35N6O3 [M+H]+ 611. found 611.

Workup

  1. customThe vial was capped
  2. customUn-reacted chloroformate was quenched
  3. customvial for an additional 3 h
  4. filtrationThe resin was filtered
  5. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-d81e9e1f46e24621a3da3ecfc8a6076e
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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