HCID 49841325, compound → HCID 49841329, compound

HRID 731749Notes

Reaction equation

HRID 731749 reaction equation
C1(NC(N)=N)CC1.[CH:8]([NH:11][C:12]1[N:17]=[C:16]([C:18]2[C:19]([CH:27]([CH3:29])[CH3:28])=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)[CH:15]=[CH:14][N:13]=1)([CH3:10])[CH3:9]>>[CH:8]1([NH:11][C:12]2[N:17]=[C:16]([C:18]3[C:19]([CH:27]([CH3:29])[CH3:28])=[N:20][N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=34)[CH:15]=[CH:14][N:13]=2)[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 49841325HCID 49841325, compoundHCID 178512453HCID 178512453, compound

Product 1

HCID 49841329HCID 49841329, compound

Procedure

Cyclopropyl-[4-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-pyrimidin-2-yl]-amine was prepared from 3-dimethylamino-1-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-propenone and N-cyclopropyl-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 (34 mg, 7%). 1H-NMR (250 MHz, DMSO-d6) δ 8.86 (d, J=6.8 Hz, 1H), 8.57 (d, J=8.3 Hz, 1H), 8.27 (d, J=6.5 Hz, 1H), 7.59 (t, J=7.9 Hz, 1H), 7.19-7.10 (m, 2H), 4.62 (broad s, 1H), 3.86-3.78 (m, 1H), 2.80-2.72 (m, 1H), 1.38 (d, J=6.5 Hz, 6H), 0.90-0.84 (m, 2H), 0.70-0.64 (m, 2H); LC/MS 294.2 m/z (M+H+). Compound 1136.

Workup

  1. customwas used in the place of recrystallization (34 mg, 7%)

Sources & evidence

ORD record
ord-e81639eafea54d438fe2018ea9eae28e
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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