3-Pyridinecarboxaldehyde → HCID 118272473, compound

HRID 590861Notes

Reaction equation

HRID 590861 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[NH2:9][C:10]1[C:14]2[CH:15]=[N:16][C:17]([NH:19][C:20]([NH:22][C@@H:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:24])=[O:21])=[CH:18][C:13]=2[N:12]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:11]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.C(Cl)Cl.C(O)C(N)(CO)CO>[C:25]1([C@H:23]([NH:22][C:20]([NH:19][C:17]2[N:16]=[CH:15][C:14]3[C:10]([NH:9][CH2:1][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=4)=[N:11][N:12]([C:31]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:13]=3[CH:18]=2)=[O:21])[CH3:24])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 118271680HCID 118271680, compound

Product 1

HCID 118272473HCID 118272473, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 6503Tris(hydroxymethyl)aminomethaneSolvent

Procedure

To an 8 mL vial charged with nicotinaldehyde (30 mg, 0.278 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 methanol (1 ml) and acetic acid (0.1 ml). The vial was capped and the contents stirred at room temperature for 2 h. Sodium cyanoborohydride (10.5 mg, 0.167 mmol) was added and the reaction mixture stirred for an additional 16 h. The reaction mixture was diluted with DCM (1 mL), trisamine MP-resin (274 mg, 0.557 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)-1-(1-phenylethyl)-3-(3-((pyridin-3-ylmethyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea, which was taken forward without purification. MS ESI calc'd. For C40H36N7O [M+H]+ 630. found 630.

Workup

  1. customThe vial was capped
  2. stirringthe reaction mixture stirred for an additional 16 h
  3. additionadded
  4. stirringthe contents of the vial shaken at room temperature for 3 h
  5. filtrationThe resin was filtered
  6. washwashed through with DCM (1 mL)
  7. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-7c4c1618e7264e65aa39c964d176ae86
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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