Bromomethylcyclopropane → 3-(1-(Cyclopropylmethyl)-1H-pyrazol-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1H-pyrazolo[4,3-c]pyridine

HRID 1046495Notes

Reaction equation

HRID 1046495 reaction equation
I[C:2]1[C:6]2[C:7]([O:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][CH:9]=[CH:10][C:5]=2[N:4](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:3]=1.N1C=C([C:42]2[C:46]3C(OC4CCOCC4)=NC=C[C:45]=3[N:44]([C:58]([C:71]3[CH:76]=[CH:75]C=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:43]=2)C=N1.BrCC1CC1>>[CH:71]1([CH2:58][N:44]2[CH:45]=[C:46]([C:2]3[C:6]4[C:7]([O:11][CH:12]5[CH2:13][CH2:14][O:15][CH2:16][CH2:17]5)=[N:8][CH:9]=[CH:10][C:5]=4[NH:4][N:3]=3)[CH:42]=[N:43]2)[CH2:76][CH2:75]1

Participants

4

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 66826813HCID 66826813, compoundHCID 1363523223-(1H-pyrazol-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 569422183-(1-(Cyclopropylmethyl)-1H-pyrazol-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1H-pyrazolo[4,3-c]pyridineYield 71%

Procedure

Prepared by a procedure analogous to Example 86 using 3-iodo-4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine as starting material and by reacting 3-(1H-pyrazol-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine with (bromomethyl)cyclopropane to give the title compound (45.5 mg, 71% over two steps). LC-MS (Method G): m/z=340.1 [M+H]+; 3.63 min. 1H-NMR (400 MHz, DMSO): δ 13.27 (s, 1H), 8.28 (s, 1H), 8.01 (s, 1H), 7.83 (d, J=5.9, 1H), 7.07 (d, J=6.0, 1H), 5.53-5.43 (m, 1H), 4.06 (d, J=7.0, 2H), 3.95-3.85 (m, 2H), 3.53 (t, J=10.3, 2H), 2.20-2.10 (m, 2H), 1.86-1.72 (m, 2H), 1.35-1.24 (m, 1H), 0.62-0.53 (m, 2H), 0.45-0.38 (m, 2H).

Sources & evidence

ORD record
ord-49b9dbf0c78c4bf79b713234561a507f
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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