Morpholine → 5-Chloro-N2-(2,5-dimethyl-4-(1-(3-morpholinopropylsulfonyl)piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 1897706Notes

Reaction equation

HRID 1897706 reaction equation
[Cl:1][C:2]1[C:3]([NH:30][C:31]2[CH:35]=[C:34]([CH3:36])[NH:33][N:32]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]3[CH2:21][CH2:20][N:19]([S:22]([CH2:25][CH2:26][CH2:27]Cl)(=[O:24])=[O:23])[CH2:18][CH2:17]3)=[CH:11][C:10]=2[CH3:29])=[N:6][CH:7]=1.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>>[Cl:1][C:2]1[C:3]([NH:30][C:31]2[CH:35]=[C:34]([CH3:36])[NH:33][N:32]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]3[CH2:21][CH2:20][N:19]([S:22]([CH2:25][CH2:26][CH2:27][N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)(=[O:24])=[O:23])[CH2:18][CH2:17]3)=[CH:11][C:10]=2[CH3:29])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 671555715-chloro-N2-(4-(1-(3-chloropropylsulfonyl)piperidin-4-yl)-2,5-dimethylphenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Product 1

HCID 446119025-Chloro-N2-(2,5-dimethyl-4-(1-(3-morpholinopropylsulfonyl)piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Procedure

The product from Step 1 was stirred in neat morpholine (0.5 mL) at 100° C. in a sealed vial for one hour. The reaction was purified by RP-HPLC to give 5-Chloro-N2-(2,5-dimethyl-4-(1-(3-morpholinopropylsulfonyl)piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as a white powder; ESMS m/z 603.2 (M+H+).

Workup

  1. customThe reaction was purified by RP-HPLC

Sources & evidence

ORD record
ord-5fad01e1515a4173a840ec60eb6a6c12
Source dataset
uspto-grants-2013_08
Patent number
US08519129B2

Reaction notes

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