1-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amine → 2-{6-(4-Chloro-benzyl)-2-[1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-ylamino]-pyrimidin-4-yl}-propan-2-ol

HRID 451429Notes

Reaction equation

HRID 451429 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)[S:4][N:3]=1.Cl[C:15]1[N:20]=[C:19]([C:21]([OH:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[N:16]=1>>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][C:17]2[N:16]=[C:15]([NH:13][CH:10]3[CH2:9][CH2:8][N:7]([C:5]4[S:4][N:3]=[C:2]([CH3:1])[N:6]=4)[CH2:12][CH2:11]3)[N:20]=[C:19]([C:21]([OH:24])([CH3:23])[CH3:22])[CH:18]=2)=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 583978761-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amineHCID 866567012-[2-Chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol

Product 1

HCID 533535222-{6-(4-Chloro-benzyl)-2-[1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-ylamino]-pyrimidin-4-yl}-propan-2-olYield 36.3%

Procedure

In analogy to example 29, 1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-ylamine (65 mg, 0.33 mmol) was reacted with 2-[2-chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol (98 mg, 0.33 mmol) to give the title compound (55 mg, 36%) as yellow foam.

Sources & evidence

ORD record
ord-9836fb63d0c4480e8b44cc1a60d9790d
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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