HCID 59624544, compound → HCID 178522302, compound

HRID 1943464Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10]3[N:11]([C:16]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[F:28])=[O:20])=[CH:17][N:18]=3)[N:12]=[C:13](Cl)[CH:14]=2)[CH:5]=[CH:4][CH:3]=1.[NH2:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([OH:36])[CH2:32][CH2:31]1>CN1C(=O)CCC1>[F:28][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:22]=1[NH:21][C:19]([C:16]1[N:11]2[N:12]=[C:13]([NH:29][C@H:30]3[CH2:35][CH2:34][C@H:33]([OH:36])[CH2:32][CH2:31]3)[CH:14]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([NH:29][C@H:30]4[CH2:35][CH2:34][C@H:33]([OH:36])[CH2:32][CH2:31]4)[N:7]=3)[C:10]2=[N:18][CH:17]=1)=[O:20]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 8-(6-bromopyridin-2-ylamino)-6-chloro-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide (40 mg, 0.086 mmol) and (trans)-4-aminocyclohexanol (100 mg, 0.868 mmol) in NMP (0.5 mL) was heated at 160° C. in a microwave for 1.5 h (300 W power). The reaction mixture was cooled to room temperature and purified by preparative reversed-phase HPLC to give 45B (39.7 mg, 62%) as yellow solid. HPLC Rt=2.780 min (Chromolith SpeedROD 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min gradient, monitored at 220 nm), [M+H]=576.

Workup

temperatureThe reaction mixture was cooled to room temperature
custompurified by preparative reversed-phase HPLC

Sources & evidence

ORD record: ord-e6d8c14240ee43189e0f862668ec1c9b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389527B2

Reaction notes

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