Acetic Acid → HCID 68734150, compound

HRID 1798498Notes

Reaction equation

HRID 1798498 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:8]=[C:7]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([C:23]4[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=4)[CH:22]=3)[CH:6]=2)[CH2:3][CH2:2]1.[C:31]([O:35][C:36](=[O:43])[NH:37][C@@H:38]1[CH2:42][CH2:41][NH:40][CH2:39]1)([CH3:34])([CH3:33])[CH3:32].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:31]([O:35][C:36](=[O:43])[NH:37][C@@H:38]1[CH2:42][CH2:41][N:40]([CH2:27][C:26]2[CH:25]=[CH:24][C:23]([C:21]3[CH:22]=[C:17]([C:7]4[CH:6]=[C:5]([NH:4][CH:1]5[CH2:2][CH2:3]5)[N:10]=[C:9]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=5)[CH:8]=4)[CH:18]=[N:19][CH:20]=3)=[CH:30][CH:29]=2)[CH2:39]1)([CH3:34])([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86633645HCID 86633645, compound

Product 1

HCID 68734150HCID 68734150, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(6′-cyclopropylamino-[2,2′;4′,3″]terpyridin-5″-yl)-benzaldehyde (Example 2.64)(1 eq, 0.204 mmol, 80 mg) in DCM (3 ml) is treated with (R)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (2.2 eq, 0.448 mmol, 83.2 mg) followed by AcOH (1.2 eq, 0.245 mmol, 0.14 ml) and sodium triacetoxyborohydride (3.1 eq, 0.632 mmol, 134 mg). The reaction mixture is stirred at room temperature overnight and then extracted with DCM. The organic portion is washed with water, dried (MgSO4) and concentrated in vacuo to afford the title compound which is used in the next step without further purification; [M+H]+ 563.

Workup

  1. extractionextracted with DCM
  2. washThe organic portion is washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c59bd0d54d2846a0b02389c0e721ddeb
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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