Carbon Tetrachloride → HCID 18446622, compound

HRID 1269056Notes

Reaction equation

HRID 1269056 reaction equation
[CH:1]1([NH:6][C:7]2[CH:12]=[C:11]([C:13]3[C:21]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH:29]([CH3:31])[CH3:30])[N:23]=4)=[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][N:15]4[N:14]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.C(Cl)(Cl)(Cl)[Cl:38]>>[Cl:38][C:20]1[N:15]2[N:14]=[C:13]([C:11]3[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:12]=3)[C:21]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH:29]([CH3:31])[CH3:30])[N:23]=3)=[C:16]2[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 18446642HCID 18446642, compoundHCID 178418339Butyllithium

Product 1

HCID 18446622HCID 18446622, compound

Procedure

In a similar manner as described in Example 17 from N-cyclopentyl-N-(4-{3-[2-(isopropylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}-2-pyridinyl)amine (155 mg, 0.375 mmol), n-butyllithium (700 μL 1.6 M in hexanes, 1.12 mmol), and carbon tetrachloride (145 μL, 1.50 mmol) was formed 4-{7-chloro-2-[2-(cyclopentylamino)-4-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl}-N-isopropyl-2-pyrimidinamine. Flash chromatography (1:1 hexanes:ethyl acetate to 1:2 hexanes:ethyl acetate) provided sample (65 mg, 39%). Rf 0.20 (1:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 8.40 (d, 1H), 8.14–8.11 (m, 2H), 7.27 (m, 1H), 7.07 (d, 1H), 6.82 (d, 1H), 6.66 (s, 1H), 6.46 (d, 1H), 5.11 (d, 1H), 4.79 (d, 1H), 4.21 (m, 1H), 3.98 (m, 1H), 1.98 (m, 2H), 1.74–1.44 (m, 6H), 1.30 (d, 6H); MS m/z 448 (M+1).

Sources & evidence

ORD record
ord-3c5cab18d84a4ad4b8f7a989fe5704b8
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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