HCID 49841325, compound → HCID 49841326, compound

HRID 731746Notes

Reaction equation

HRID 731746 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([NH2:8])=[NH:7].C(NC1N=[C:17]([C:19]2[C:20]([CH:28]([CH3:30])[CH3:29])=[N:21][N:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=23)[CH:16]=[CH:15]N=1)(C)C>>[CH:28]([C:20]1[C:19]([C:17]2[CH:16]=[CH:15][N:8]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][OH:1])[N:7]=2)=[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][N:22]2[N:21]=1)([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 49841325HCID 49841325, compoundHCID 178512982HCID 178512982, compound

Product 1

HCID 49841326HCID 49841326, compound

Procedure

3-[4-(2-Isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-pyrimidin-2-ylamino]-propan-1-ol was prepared from 3-dimethylamino-1-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-propenone and N-(3-hydroxy-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 (166 mg, 18%). 1H-NMR (250 MHz, DMSO-d6) δ 8.85 (d, J=7.0 Hz, 1H), 8.44-8.22 (m, 3H), 7.59 (t, J=7.0 Hz, 1H), 7.18-7.05 (m, 2H), 4.07 (broad s, 1H), 3.79 (sept, J=6.9 Hz, 1H), 3.58-3.33 (m, 4H), 1.77 (pent, J=6.6 Hz, 2H), 1.37 (d, J=6.5 Hz, 6H); LC/MS 312.3 m/z (M+H+). Compound 1134.

Workup

  1. customwas used in the place of recrystallization (166 mg, 18%)

Sources & evidence

ORD record
ord-f1ca62e2a6c34bc0860f569690761a2f
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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