Nitrogen → HCID 66547504, compound

HRID 1507934Notes

Reaction equation

HRID 1507934 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9]([NH:10][C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[CH3:12])=[C:8]([C:20]([NH2:22])=[O:21])[CH:7]=[N:6][N:5]2[CH:23]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N#N>O1CCOCC1>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C@H:11]([NH:10][C:9]1[C:4]2[N:5]([CH:23]=[C:2]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:3]=2)[N:6]=[CH:7][C:8]=1[C:20]([NH2:22])=[O:21])[CH3:12]

Participants

6

Reactant 4

HCID 947NitrogenHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 68292185HCID 68292185, compound2×

Product 1

HCID 66547504HCID 66547504, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-6-bromo-4-(1-(2-fluorophenyl)ethylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide (Intermediate 7, 1 equiv), phenylboronic acid (1 equiv), PdCl2(dppf)-CH2Cl2 complex (0.05 equiv) and 2M K3PO4 (3.4 equiv) in dioxane (0.5 mL) was purged with N2 then at 140° C. for 0.5 h. Following cooling to rt, the product was isolated via reverse-phase preparative HPLC (condition F) of the crude reaction mixture to afford the title compound (3.8 mg) as a brown solid. HPLC (conditions B): retention time=4.28 min; LCMS: 375.14 (M+H)+; 1H NMR (CD3OD, 400 MHz) δ 8.17 (s, 1H), 7.88 (d, J=1.7 Hz, 1H), 7.52 (d, J=7.0 Hz, 2H), 7.14-7.44 (m, 7H), 7.03 (d, J=1.8 Hz, 1H), 5.80 (q, J=6.6 Hz, 1H), 1.70 (d, J=6.6 Hz, 3H).

Workup

  1. customthe product was isolated via reverse-phase preparative HPLC (condition F) of the crude
  2. customreaction mixture

Sources & evidence

ORD record
ord-d2acc28bb90b450892c3f13da4156da4
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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