4-Chloropyrrolo[1,2-b]pyridazine-3-carboxamide → 4-(4-Hydroxycyclohexylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 1408917Notes

Reaction equation

Cl[C:2]1[C:3]2[N:4]([CH:11]=[CH:12][CH:13]=2)[N:5]=[CH:6][C:7]=1[C:8]([NH2:10])=[O:9].[NH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]1>CN1C(=O)CCC1.CO>[OH:21][CH:18]1[CH2:19][CH2:20][CH:15]([NH:14][C:2]2[C:3]3[N:4]([CH:11]=[CH:12][CH:13]=3)[N:5]=[CH:6][C:7]=2[C:8]([NH2:10])=[O:9])[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide, Preparation 3 (15 mg, 0.077 mmol) and (trans)-4-aminocyclohexanol (22.08 mg, 0.192 mmol) in NMP (0.3 ml) was heated at 80° C. for 1.5 h. The product mixture was diluted with methanol and purified by preparative HPLC (condition A) to afford the title compound as a white solid (17.8 mg, 85% yield). 1H NMR (400 MHz, MeOD) δ ppm 1.44-1.56 (m, 4 H) 1.97-2.08 (m, 2 H) 2.17-2.28 (m, 2 H) 3.62-3.76 (m, 1 H) 4.03-4.19 (m, 1 H) 6.69 (dd, J=4.52, 2.76 Hz, 1 H) 6.91 (dd, J=4.77, 1.51 Hz, 1 H) 7.56 (dd, J=2.64, 1.63 Hz, 1 H) 8.10 (s, 1 H). HPLC (method F): ret. Time 2.105 min.; LC/MS [m/z, (M+H)] 275.0.

Workup

custompurified by preparative HPLC (condition A)

Sources & evidence

ORD record: ord-c1ab580619344631885155fa056a0ab6
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921368B2

Reaction notes

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