2-Aminopyridine → HCID 131727228, compound

HRID 2375830Notes

Reaction equation

HRID 2375830 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[N:8]1([C:13](N2C=CN=C2)=[O:14])C=CN=C1.[CH3:20]CN(C(C)C)C(C)C.Cl.Cl.Cl.[NH:32]1[C:40]2[C:35](=[CH:36][C:37]([NH:41][C:42]3[C:43]4[CH:50]=[C:49]([C:51]5[CH2:52][CH2:53][NH:54][CH2:55][CH:56]=5)[NH:48][C:44]=4[N:45]=[CH:46][N:47]=3)=[CH:38][CH:39]=2)[CH:34]=[N:33]1>CN(C=O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:53]1[CH2:52][C:51]([C:49]2[NH:48][C:44]3[N:45]=[CH:46][N:47]=[C:42]([NH:41][C:37]4[CH:36]=[C:35]5[C:40](=[CH:39][CH:38]=4)[NH:32][N:33]=[CH:34]5)[C:43]=3[CH:50]=2)=[CH:56][CH2:55][N:54]1[CH2:20][C:13]([NH2:8])=[O:14]

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 69275332HCID 69275332, compound

Product 1

HCID 131727228HCID 131727228, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-aminopyridine (22.6 mg, 0.24 mmol) and diimidazol-1-ylmethanone (CDI, 39 mg, 0.24 mmol) in DMF (0.75 mL) was stirred at 50° C. for 1 h. After cooling to rt, i-Pr2NEt (0.14 mL, 0.8 mmol) was added, followed by (1H-indazol-5-yl)-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine tri-HCl (88.1 mg, 0.2 mmol). The mixture was stirred at rt for 2 h and 50° C. for 3 h. The resulting mixture was filtered and submitted to mass-directed HPLC purification to yield the title compound. 1H-NMR(CD3OD, 400 MHz): δ=2.66 (m, 2H), 3.88 (t, J=6.0 Hz, 2H), 4.37 (m, 2H), 6.45 (s, 1H), 6.71 (s, br, 1H), 7.38 (t, J=6.0 Hz, 1H), 7.48 (dd, J=2.0, 9.2 Hz, 1H), 7.66 (d, J=8.8 Hz, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.98 (d, J=1.2 Hz, 1H), 8.16 (d, J=12.4 Hz, 1H), 8.22 (dt, J=1.6, 8.8 Hz, 1H). 8.29 (d, J=6.0 Hz, 1H). MS (ES+): m/z 451.95 [MH+]. HPLC: tR=1.77 min (ZQ2000, polar—5 min).

Workup

  1. filtrationThe resulting mixture was filtered
  2. customsubmitted to mass-directed HPLC purification

Sources & evidence

ORD record
ord-40649c0d9bf842008aecb78d769f89d8
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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