Sodium Bicarbonate → HCID 178515533, compound

HRID 1674670Notes

Reaction equation

C[O:2][C:3]1[N:4]=[N:5][C:6]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:32]=[C:31]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=5)[NH:30][N:29]=4)[CH2:24][CH2:23]3)=[CH:17][CH:16]=2)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1.Cl.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>O>[C:9]1([C:7]2[CH:8]=[C:3]([OH:2])[N:4]=[N:5][C:6]=2[C:15]2[CH:16]=[CH:17][C:18]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:32]=[C:31]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=5)[NH:30][N:29]=4)[CH2:24][CH2:23]3)=[CH:19][CH:20]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 3-methoxy-5-phenyl-6-(4-{[4-(5-pyridin-2-yl-1H-pyrazol-3-yl)piperidin-1-yl]methyl}phenyl)pyridazine (2-3) TFA (36.8 mg, 0.059 mmol) and pyridine hydrochloride (591 mg, 5.1 mmol) was heated at 150° C. for 5 min. This solid was dissolved in water, the solution made basic with NaHCO3, and the product extracted into methylene chloride/methanol (5%). This solution was dried, filtered and the solvents evaporated. This residue was digested in acetonitrile to give 5-phenyl-6-(4-{[4-(5-pyridin-2-yl-1H-pyrazol-3-yl)piperidin-1-yl]methyl}phenyl)pyridazin-3-ol (2-4) as a tan solid freebase. NMR (CDCl3/CD3OD): δ8.66 (1H, br d, J=4.5 Hz), 8.40 (1H, br d, J=7 Hz), 8.29 (1H, br m), 7.67 (2H, br m), 7.55 (2H, d, J=7.5 Hz), 7.42 (1H, s), 7.35 (1H, t, J=7.5 Hz), 7.11-7.30 (4H, m), 7.08 (2H, d, J=9 Hz), 6.98 (1H, s), 4.21 (2H, s), 3.47 (2H, d, J=10 Hz), 3.26 (1H, m), 3.00 (2H, m), 2.43 (2H, br d, J=11 Hz), 2.13 (2H, m); m/e (m+1): 489.2.

Workup

extractionthe product extracted into methylene chloride/methanol (5%)
customThis solution was dried
filtrationfiltered
customthe solvents evaporated

Sources & evidence

ORD record: ord-5169a5c6388d4fb39f137d336f736d5c
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003643B2

Reaction notes

Loading…