Acetic Acid → USRE48711, Example 234

HRID 389631

Reaction equation

[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([NH:27][NH2:28])=O)[N:20]=4)=[O:17])[CH:11]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[CH3:29]N(C)C=O.CN(C)C(=O)C.[CH3:40][O:41][CH2:42][C@@H:43]([NH2:45])[CH3:44].C(O)(=O)C>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]5[N:45]([C@@H:43]([CH3:44])[CH2:42][O:41][CH3:40])[CH:29]=[N:28][N:27]=5)[N:20]=4)=[O:17])[CH:11]=3)=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 6-cyclopropyl-N-(6-(hydrazinecarbonyl)pyridin-2-yl)-3,4′-bipyridine-2′-carboxamide, a compound of formula (3) (75 mg, 0.20 mmol) in toluene (0.20 M) was added N,N-dimethylformamide/N,N-dimethylacetamide (67 μL, 0.50 mmol), (S)-2-methoxy-1-methyl-ethylamine (72 mg μL, 0.80 mmol), and acetic acid (11 μL, 0.20 mmol). The reaction was heated to 150° C. for 30 minutes in a microwave reactor. The reaction mixture was concentrated under reduced pressure, and the residue suspended in acetonitrile/diethyl ether (15 mL, 1:1 ratio), filtered and washed with acetonitrile/diethyl ether (2×10 mL). The solid thus obtained was dried under reduced pressure to afford 57 mg (63% yield) of (S)-6-cyclopropyl-N-(6-(4-(1-methoxypropan-2-yl)-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-3,4′-bipyridine-2′-carboxamide as a white solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
filtrationfiltered
washwashed with acetonitrile/diethyl ether (2×10 mL)
customThe solid thus obtained
customwas dried under reduced pressure

Sources & evidence

ORD record: ord-b93c6149546e4fd0b5540490a1966609
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378108B2

Linked notes

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