6-(chloromethyl)-N,N-dimethylpyridin-2-amine → 5-benzyloxy-N-({1-[(6-(dimethylamino)pyridin-2-yl)methyl]pyrazol-4-yl}methyl)-N-(6-methoxypyridin-3-yl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide

HRID 218808Notes

Reaction equation

HRID 218808 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH:14]2[C:19]([N:21]([C:28]1[CH:29]=[N:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=1)[CH2:22][C:23]1[CH:24]=[N:25][NH:26][CH:27]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:37][C:38]1[N:43]=[C:42]([N:44]([CH3:46])[CH3:45])[CH:41]=[CH:40][CH:39]=1>>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH:14]2[C:19]([N:21]([CH2:22][C:23]1[CH:24]=[N:25][N:26]([CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[C:42]([N:44]([CH3:46])[CH3:45])[N:43]=2)[CH:27]=1)[C:28]1[CH:29]=[N:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 178543736-(chloromethyl)-N,N-dimethylpyridin-2-amineHCID 595974155-benzyloxy-N-(6-methoxypyridin-3-yl)-N-[(pyrazol-4-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide

Product 1

HCID 595972685-benzyloxy-N-({1-[(6-(dimethylamino)pyridin-2-yl)methyl]pyrazol-4-yl}methyl)-N-(6-methoxypyridin-3-yl)-1,2,3,4-tetrahydronaphthalene-1-carboxamideYield 25.6%

Procedure

By the reaction and treatment in the same manner as in Example 271 using 5-benzyloxy-N-(6-methoxypyridin-3-yl)-N-[(pyrazol-4-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.94 g) and 6-chloromethyl-2-(dimethylamino)pyridine (0.68 g) as starting materials, 5-benzyloxy-N-({1-[(6-(dimethylamino)pyridin-2-yl)methyl]pyrazol-4-yl}methyl)-N-(6-methoxypyridin-3-yl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.31 g) was obtained. 1H-NMR (CDCl3) δ: 1.38-1.67(1H,m), 1.73-2.07(3H,m), 2.61-2.82(2H,m), 3.04(6H,s), 3.59-3.72(1H,m), 3.93(3H,s), 4.64(1H,d,J=14.4 Hz), 4.83(1H,d,J=14.4 Hz), 5.03(2H,s), 5.21(2H,s), 6.18(1H,d,J=7.2 Hz), 6.40(1H,d,J=8.4 Hz), 6.54(1H,d,J=7.5 Hz), 6.62-6.76(2H,m), 7.01(1H,t,J=8.0 Hz), 7.21-7.52(9H,m), 7.99(1H,d,J=2.4 Hz).

Sources & evidence

ORD record
ord-0b8c6c12c04d4d69b6728d323ed047e3
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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