Diisopropylethylamine → HCID 89554298, compound

HRID 1507546Notes

Reaction equation

HRID 1507546 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[C:14]([NH:25][C@@H:26]4[CH2:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:27]4)=[N:15][C:16](S(C)(=O)=O)=[N:17][C:18]=3[O:19][CH3:20])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH:40]=1.C(N(C(C)C)C(C)C)C>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[C:14]([NH:25][C@@H:26]4[CH2:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:37])([CH3:38])[CH3:36])=[O:33])[CH2:27]4)=[N:15][C:16]([N:48]4[CH2:49][CH2:50][N:45]([C:41]5[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=5)[CH2:46][CH2:47]4)=[N:17][C:18]=3[O:19][CH3:20])[S:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4372341-(Pyridin-3-yl)piperazineHCID 117683818HCID 117683818, compound

Product 1

HCID 89554298HCID 89554298, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl (3R)-3-([5-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-2-methanesulfonyl-6-methoxypyrimidin-4-yl]amino)piperidine-1-carboxylate (45.0 mg, 0.08 mmol, 1.00 equiv), 1-(pyridin-3-yl)piperazine (15.6 mg, 0.10 mmol, 1.20 equiv) and N-ethyl-N-isopropylpropan-2-amine (20.7 mg, 0.16 mmol, 2.00 equiv) in CH3CN (6.0 mL) was heated for 15 h at 100° C. in an oil bath. Concentration under reduced pressure gave 80.0 mg (crude) of the title compound, which was used directly for next step without further purification. MS m/z [M+H]+ (ESI): 647.

Workup

  1. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-0ddc4214a3954514a04ea5dee0f8731f
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

Loading…