Tert-Butylamine → HCID 67248257, compound

HRID 1190922Notes

Reaction equation

HRID 1190922 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[C:18]([CH2:20]O)[CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[C:32]([NH2:36])([CH3:35])([CH3:34])[CH3:33]>CN1C(=O)CCC1.C(Cl)Cl>[C:32]([NH:36][CH2:20][C:18]1[CH:19]=[C:14]([NH:13][C:7]2[C:6]3[C:11](=[CH:12][C:3]([Cl:2])=[CH:4][CH:5]=3)[N:10]=[CH:9][CH:8]=2)[CH:15]=[CH:16][C:17]=1[N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1)([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 24386Thionyl ChlorideHCID 67247174HCID 67247174, compound2×

Product 1

HCID 67248257HCID 67248257, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a suspension of {5-[(7-chloroquinolin-4-yl)amino]-2-(morpholin-4-yl)phenyl}methanol hydrochloride (compound of step C of example 31) (0.105 g, 0.26 mmol) in 4 mL of NMP at 0° C. was added thionyl chloride (90 μL, 1.23 mmol). The reaction mixture was warmed up to room temperature and stirred for 3 h. The reaction mixture was then slowly added to tert-butylamine (0.81 mL, 7.75 mmol) in 1 mL of NMP at 0° C. and then stirred at room temperature for 2 h. This solution was diluted in 100 mL of CH2Cl2 and washed with a saturated aqueous solution of NaHCO3. The organic layer was dried over MgSO4, filtered, evaporated and purified by flash chromatography (Et2O/MeOH/NH4OH//90/10/1 then 80/20/1) to yield expected compound as a yellow solid (103 mg, 92% yield). LC-MS: m/z (ESI) 425.2 [M+H]+.

Workup

  1. stirringstirred at room temperature for 2 h
  2. washwashed with a saturated aqueous solution of NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by flash chromatography (Et2O/MeOH/NH4OH//90/10/1

Sources & evidence

ORD record
ord-ec8a14aff8cd4392ba7541dfd4f07248
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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