Diisopropylethylamine → HCID 46182991, compound

HRID 1028074Notes

Reaction equation

HRID 1028074 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([NH:8]C(=O)OC(C)(C)C)[CH2:3]1.FC(F)(F)S(O[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]4[S:39][CH:40]=[CH:41][N:42]=4)[N:33]=3)[CH:30]=2)[N:25]=[CH:24][CH:23]=1)(=O)=O.CCN(C(C)C)C(C)C>CC(O)C>[CH3:1][C@H:2]1[CH2:7][N:6]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([C:38]5[S:39][CH:40]=[CH:41][N:42]=5)[N:33]=4)[CH:30]=3)[N:25]=[CH:24][CH:23]=2)[CH2:5][C@@H:4]([NH2:8])[CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57433105tert-Butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamateHCID 86656458HCID 86656458, compound

Product 1

HCID 46182991HCID 46182991, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of tert-butyl (3S,5R)-5-methylpiperidin-3-ylcarbamate (1.5 equiv.) and 6-(6-(thiazol-2-yl)pyridin-2-yl)quinolin-4-yl trifluoromethanesulfonate (1.0 equiv.) and DIEA (2.0 equiv.) in i-PrOH was heated in a microwave at 150° C. (5×20 min). Upon cooling the material was purified directly by RP-HPLC. Upon lyophilization, the Boc group was deprotected by treatment with 25% TFA/CH2Cl2, concentrated, purified by RP-HPLC and lyophilized to yield (3S,5R)-5-methyl-1-(6-(6-(thiazol-2-yl)pyridin-2-yl)quinolin-4-yl)piperidin-3-amine (51%). LC/MS=402.0 (M+H), LC=2.16 min.

Workup

  1. temperatureUpon cooling the material
  2. customwas purified directly by RP-HPLC
  3. concentrationconcentrated
  4. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-daffed18c2f34fdea0ce59db66e287f8
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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