Morpholine → HCID 59506920, compound

HRID 1800599Notes

Reaction equation

HRID 1800599 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([O:15][C:16]1[CH:17]=[C:18]([NH:23][C:24](=[O:36])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([C:34]#[N:35])([CH3:33])[CH3:32])[CH:26]=3)[CH:19]=[CH:20][C:21]=1[CH3:22])[N:9]=2)=[O:4].[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.C(N(CC)CC)C>O1CCCC1>[C:34]([C:31]([C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[C:24]([NH:23][C:18]1[CH:19]=[CH:20][C:21]([CH3:22])=[C:16]([O:15][C:10]2[N:9]=[C:8]3[S:7][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)=[N:14][C:13]3=[CH:12][CH:11]=2)[CH:17]=1)=[O:36])([CH3:32])[CH3:33])#[N:35]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 86646041HCID 86646041, compound

Product 1

HCID 59506920HCID 59506920, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-[3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]-3-(1-cyano-1-methylethyl)benzamide (304 mg, 0.584 mmol) produced in Example C15(i) in tetrahydrofuran (5 mL) were added morpholine (78.8 μL, 0.901 mmol) and triethylamine (125 μL, 0.901 mmol), and the mixture was stirred at 60° C. for 4 hr. The title compound (141 mg, 55%) was obtained as white crystals by operation in the same manner as in Example C88. The present compound was recrystallized from ethyl acetate and tetrahydrofuran.

Sources & evidence

ORD record
ord-922e4dfef5f44d8ba90dde26c4d73ebf
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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