HCID 49841325, compound → HCID 49841328, compound

HRID 731748Notes

Reaction equation

HRID 731748 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[NH:13])[CH2:4][CH2:3]1.C(NC1N=[C:23]([C:25]2[C:26]([CH:34]([CH3:36])[CH3:35])=[N:27][N:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=23)[CH:22]=[CH:21]N=1)(C)C>>[CH:34]([C:26]1[C:25]([C:23]2[CH:22]=[CH:21][N:14]=[C:12]([NH:11][CH2:10][CH2:9][CH2:8][N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[N:13]=2)=[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][N:28]2[N:27]=1)([CH3:36])[CH3:35]

Participants

3

Reactant 2

HCID 49841325HCID 49841325, compoundHCID 178480876HCID 178480876, compound

Product 1

HCID 49841328HCID 49841328, compound

Procedure

[4-(2-Isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-pyrimidin-2-yl]-[3-(4-methyl-piperazin-1-yl)-propyl]-amine was prepared from 3-dimethylamino-1-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-propenone and N-[3-(4-methyl-piperazin-1-yl)-propyl]-guanidine following the method used in Step 4 of the synthesis of Isopropyl-[4-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-pyrimidin-2-yl]-amine (Example 66), except preparative-HPLC purification was used in the place of recrystallization (162 mg, 19%). 1H-NMR (250 MHz, DMSO-d6) δ 8.72 (d, J=6.8 Hz, 1H), 8.28-8.20 (m, 2H), 7.37 (t, J=7.8 Hz, 1H), 7.16-7.10 (m, 1H), 6.99 (t, J=6.6 Hz, 1H), 6.80 (d, J=7.3 Hz, 1H), 3.78 (sept, J=7.3 Hz, 1H), 2.56-2.32 (m, 10H), 2.22 (s, 3H), 2.10-2.06 (m, 2H), 1.73 (pent, J=6.9 Hz, 2H), 1.35 (d, J=6.8 Hz, 6H); LC/MS 394.3 m/z (M+H+). Compound 1135.

Workup

  1. customwas used in the place of recrystallization (162 mg, 19%)

Sources & evidence

ORD record
ord-70884615d78f40d2a19cd23c6cba4153
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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