Ammonia methanol → HCID 58020182, compound

HRID 1632035Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[C:16]([F:30])=[C:17]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=4)[C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)=[CH:10][N:9]2[CH:31]=1)=O)C.[NH3:32].CO>>[Cl:29][C:25]1[CH:24]=[C:23]([C:17]2[C:18]([O:21][CH3:22])=[CH:19][CH:20]=[C:15]([CH2:14][C:11]3[CH:12]=[CH:13][C:8]4[N:9]([CH:31]=[C:6]([C:4]([NH2:32])=[O:3])[N:7]=4)[CH:10]=3)[C:16]=2[F:30])[CH:28]=[CH:27][CH:26]=1

Participants

Reactant 2

HCID 21705897Ammonia methanol

HCID 57703746HCID 57703746, compound

Product 1

HCID 58020182HCID 58020182, compoundYield 71%

Conditions

Temperature: 60 °C

Procedure

Into an 8 mL vial was added 6-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester (I-37) synthesized above (37 mg, 0.084 mmol) and 2 mL of 7N NH3/MeOH. After stirring for 20 hours at 60° C., the reaction was concentrated. Trituration with ether provided 6-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-imidazo[1,2-a]pyridine-2-carboxylic acid amide (P-429) (24.5 mg, 71%) as a white solid. 1H-NMR (400 MHz, DMSO-d6): 8.42 (s, 1H), 8.30 (s, 1H), 7.64 (br s, 1H), 7.53 (d, J=4.6 Hz, 1H), 7.42 (m, 5H), 7.30 (m, 1H), 7.23 (dd, 1H, J=9.6, 1.6 Hz), 6.97 (d, 1H), 8.4 Hz), 3.95 (s, 2H), 3.74 (s, 3H) ppm. LC/MS=83.4%, 410.0 (APCI+).

Workup

concentrationthe reaction was concentrated

Sources & evidence

ORD record: ord-bedb09e56ede4acd9728fd74b9c77b0b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791267B2

Reaction notes

Loading…