Dimethylformamide → Diisopropylethylamine

HRID 2044080Notes

Reaction equation

ClC1[CH:10]=[C:9]([NH:11][C:12]2C=CC(C(N3CCOCC3)=O)=C[CH:13]=2)[C:5](C(O)=O)=CN=1.[NH4+].[OH-].O1[CH2:33][CH2:32]OCC1.[CH3:34]N(C=O)C>>[CH3:13][CH2:12][N:11]([CH:32]([CH3:33])[CH3:34])[CH:9]([CH3:10])[CH3:5]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 14923Ammonium Hydroxide

HCID 312751,4-Dioxane

HCID 574896306-Chloro-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinic acid

Product 1

HCID 81531Diisopropylethylamine

Procedure

A mixture of 6-chloro-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinic acid (280 mg, 0.774 mmol) in DMF (10 mL) was treated with NH4OH 0.5 M solution in dioxane (7.74 mL, 3.87 mmol) and DIEA (0.676 mL, 3.87 mmol) to give a cloudy suspension. Then added HATU (589 mg, 1.548 mmol) and stirred at rt for 24 hrs. Diluted with water and extracted into ethyl acetate and washed with 10% LiCl and concentrated to give 230 mg of 6-chloro-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide as a white solid. LCMS: (M+H)+=361.03, 363.02 (Cl pattern).

Sources & evidence

ORD record: ord-612e41eb3e7f4e31a655f20e59dab8d0
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586751B2

Reaction notes

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