Acetic Acid → HCID 68734971, compound

HRID 1878598Notes

Reaction equation

HRID 1878598 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:9]=[C:10]([C:17]3[CH:18]=[C:19]([C:23]4[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=4)[CH:20]=[N:21][CH:22]=3)[C:11]3[CH:16]=[CH:15][NH:14][C:12]=3[N:13]=2)[CH:5]=[CH:4][CH:3]=1.Cl.[CH3:32][NH2:33].CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:32][NH:33][CH2:27][C:26]1[CH:29]=[CH:30][C:23]([C:19]2[CH:20]=[N:21][CH:22]=[C:17]([C:10]3[C:11]4[CH:16]=[CH:15][NH:14][C:12]=4[N:13]=[C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=4)[N:9]=3)[CH:18]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 86632431HCID 86632431, compound2×

Product 1

HCID 68734971HCID 68734971, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-{5-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyridin-3-yl}-benzaldehyde (Intermediate 58) (1 eq, 0.243 mmol, 100 mg) and methylamine hydrochloride (Sigma-Aldrich, St. Louis, USA) (1 eq, 0.243 mmol, 16.7 mg) in DCM (1 ml) is added AcOH (1.1 eq, 0.267 mmol, 15.3 ul). The solution is stirred for 5 min, then NaBH(OAc)3 (1.05 eq, 0.255 mmol, 57 mg) is added. After stirring the resulting mixture at r.t. for 1.5 h the solvents are removed in vacuo. The residue is taken up in aqueous NaHCO3 solution and extracted with DCM. The organic layer is washed with brine, dried over MgSO4, and filtered. The solvents are removed in vacuo and purification of the residue by reversed phase HPLC is yielding the title compound; [M+H]+=407; 1H-NMR (400 MHz, CDCl3): δ 12.52 (s, 1H), 9.43 (s, 1H), 8.95 (s, 1H), 8.73 (s, 1H), 8.66 (d, 1H), 7.83 (t, 1H), 7.64 (d, 2H), 7.49-7.46 (m, 3H), 7.32 (d, 1H), 6.88 (d, 1H), 3.86 (s, 2H), 2.75 (s, 3H), 2.56 (s, 3H).

Workup

  1. stirringAfter stirring the resulting mixture at r.t. for 1.5 h the solvents
  2. customare removed in vacuo
  3. extractionextracted with DCM
  4. washThe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvents are removed in vacuo and purification of the residue by reversed phase HPLC

Sources & evidence

ORD record
ord-f711cbd20d2242499061958fca4b8c7e
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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